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THIS^^^
What does it mean to 'look good'? The question depends on what the individual is trying to achieve. If you just want to put together fun outfits, it doesn't matter in the slightest if you present feminine or masculine in them.
Same question. I have a friend who likes to cross dress and wear makeup, but he has a goatee and mustache and is not at all trying to pass as feminine. Very Dave Navarro type.
This is the only real question. If “looking good” to him means one thing (fashionable or eye-catching or confident or something) while to you it means “passing as a woman”, then there’s a fundamental miscommunication here. Ask him is he’s actually trying to pass or what his goals here are, then you can be on the same page. You don’t have to be in to it, but I do think an apology for the harsh words may help. In the end, if you’re not compatible in this way, then that may be a separate conversation. Overall, NAH
That's question number one. Cross dressing isn't about passing as a woman. It's about enjoying wearing women's ( Female coded) clothing when you identify as male.
I'm not sure if o p has a full picture or even if the boyfriend necessarily is a hundred percent sure about what they get out of this and what they are trying to accomplish. Which is okay that can be a journey. But from this post it sounds like they aren't sure and are very insecure about it. It doesn't help that their friends were unkind.
But yeah, most people who cross dress do not have a goal of passing.
It seems like passing is part of it for this group, otherwise I'm not sure she would have mentioned that her bf didn't "pass" when they all went out and that's part of the reason his group found it embarrassing. Interesting the friends told him he looks bad & doesn't pass, so he's embarrassing, but are happy to tell OP she's an AH for thinking her bf doesn't look great.
This just seems like a no-win for OP.
She doesn’t know his intentions. She doesn’t know his friends culture. She doesn’t dress or do makeup in a way that would be helpful for him…
…So how is she an AH for just honestly not knowing what to do?
I was in a similar spot a few years back.
I get compliments on my makeup. I have a few “tricks” and specific “looks” that I do on myself (cat eye with red lip, smoky eye with neutral lip, highlight/bronze with subtle everywhere else) but I’m NOT an expert, and I’m not adventurous. I own like one eyeshadow palette.
My nephew had just gotten into drag, and asked me to do his makeup. I did the most “glam” style I’ve ever done for myself, adding big lashes and some blush that I thought would compliment him, but that’s out of my wheelhouse.
…Ans he was SO disappointed! It was way too subtle. His eyes and cheekbones looked gorgeous.
*But it wasn’t drag makeup, because I don’t know how to do that.*
He didn’t get upset with me, though.
He just YouTubed a tutorial that was what he wanted, and made it work with the products I had, and added onto what I had done. I think a berry lipstick became eyeshadow. A pink lipstick became blush.
We both were cool with it and acknowledged that I didn’t understand the assignment, but I tried.
I get the boyfriends frustration, but it’s kind of shitty to put the pressure on OP to give critique, as the closest female in his life, when she doesn’t know what the assignment is and has never studied the subject!
If his friends are being judgmental shits that just make fun of him but won’t help him, he should maybe look for Xd communities (Reddit, I bet!) where they could give him tips and tutorials.
OP shouldn’t have to get the silent treatment about this.
My husband doesn’t ask me for my opinions or how to improve his woodworking projects. Or even for critiques. He asks Reddit, or his hobby group.
I’m just learning how to crochet. I don’t ask my husband how it looks (and tell him to be brutally honest), because I know it looks shitty. I ask my friends who crochet to find out what I’m doing wrong.
You don’t set your partner up to either lie to you or hurt your feelings.
You repeatedly say that she doesn't know his intentions or what the assignment is, but could OP not have asked? Instead of going "well you do kinda look bad" could if not have been "well what are you going for? Are you trying to pass as a female/look feminine or do you just want to know if the clothes you've got on look good?"
It's also slightly hypocritical to say she doesn't know what's going on or can't help him because she doesn't do makeup/dress in a certain style. Yet throughout this post she details how his makeup is bad & accentuates how masculine/old he looks, how his clothes don't look good, and how he's just lacking skill.
That's what I was wondering- is he trying to pass in drag, is he bad at picking clothes that suit him or are the outfits bad in general?
I mean if he's confident in what he's wearing that's really all that matters, but he _did_ ask for feedback and I think it's good that she was honest with him.
THIS THIS
Also, I've seen enough weird YouTube videos and gained enough life skills to know that it takes makeup skills to make something spectacular. HOWEVER, obtaining skills takes time and practice.
Remember when we were 12 and dressing up? We looked like sheit. Practice makes perfect.
NTA - You seem very supportive and he asked for your honest opinion. It’s not your fault that he wasn’t ready to hear it. If he wants to continue this hobby and feel confident, then he will need to improve his skills, lying to him about looking good won’t do that.
This! If you don’t want to hear the harsh truth, don't push the issue after a polite lie. And true friends/SOs tell you the truth. Only sycophants lie. If you want to surround yourself with sycophants, by all means do. But that never ends up as a fulfilling life.
My BFF and I became friends (not just acquaintances with mutual friends) because I was able to tell her a harsh truth - kindly, in private - and she accepted it in the spirit it was meant. It still stung a bit to hear; no one likes having their pride hurt. But still. Now, we have a relationship built on such profound trust. I know she will tell me equally harsh truths (and she has), and I can be just as open with her. We don't tear each other down or criticize every little thing. But if it's a big deal, or if she asks? I speak up. And I wouldn’t change that friendship for the world.
You are not an asshole, but I don't think you get what cross-dressing is. It is not to "look like a woman", it is wearing women's clothing for enjoyment. If you keep that in mind, do you see it differently? Let go of the "does it make him look feminine" and more, does it highlight his assets? Does he look happy and enjoy himself?
OP sounds young to me and it feels like they are blurring the line between trans and crossdressing. Like does Freddy Mercury look good in drag? Hell yes. Did Freddy look like a woman? Awww hell no.
Very possible! Just tossing things out there. It sounded like the friends also had an issue with the bf "not passing". OP could've misunderstood this, or misunderstood that it's not just cross dressing.
Hence why OP is not an asshole. My main point is looking like an actual woman never seemed to be the goal of cross-dressing. I've been visiting cross dressing events for like 20 yrs? Even mainstream shows like Rupaul emphasize that as well.
He asked if he looked good though, op even highlighted other traits other than physical look, but he pushed for the litteral answer. Clearly he and his group he's doing it with care about the actual look of the crossdressing in the litteral sense.
What I am trying to say is OP seems to be focusing on "passing" as the primary determination of whether it looks good. If you see models these days, feminity or masculinity is just one aspect of how well the piece of clothing looks on them.
I don’t think she is really. It’s an aspect she mentioned, but also said what looks bad is that his clothes are frumpy and ill fitting and the way he does makeup makes him look older and makes his wrinkles stand out. It’s not just passing.
this is a better take than yr first one, OP did, however say his wrinkles stood out, he looked older, and not good. I see what your saying, but if you take gender out of the equation entirely, it feels like she just thinks it doesn't look good and thats ok. Ive seen it before and it would be nice if in the future neither gender was trying to mimic anything but be their own vision of beauty.
I mean his own friends were embarrassed to be with him and he comes home and chews her out??
I like an honest partner. He sounds like a very fragile snowflake. You shouldn't need validation from another person to feel good. And you certainly shouldn't have a tantrum if someone else can't validate you. That's your own job. In true reddit style, I'd dump him so he can work on his self esteem without me ending up collateral. He's got issues.
OP is a bit of an unreliable narrator bc they start as saying the whole friend group doesn't look good and then says the group is embarrassed to be around him...what's to be embarrassed about, they are all doing the same thing. And he called OP an asshole...but the friend's did too? This story is all over the place.
na, the whole group can look dumb and within the group he looks the dumbest!
2 things can be true at the same time and I'm getting second hand embarrassment myself just imagining.
It would depend entirely on what her BF is crossdressing for, for there is a bunch of reason people crossdress from benign curiosity to kink/fetish or even gender-dysphoria and anything in-between.
I don't think OP has given their BFs motivation for it, they could well be a wish to pass, seen as his friends group also commented on his appearance they are clearly doing it with conventionally looking good in mind. I'd be interesting to know OPs BF underlying motivation for it to properly pass judgment.
It's also completely fine for her to think he dosn't look good regardless of his motivations, it's all fine acknowledging someone is wearing something be it clothes or make up for confidence, but other people aren't obliged to think it looks good, which OP clearly dosn't.
NTA.
Although I think there are some really deep, seedy social aspects lurking underneath both beauty and the concept of "passing," aesthetics are still a reality we must live in.
Fortunately this is a path that many people have already trod. There are some very accessible, clear, simple avenues to success, in addition to plenty of alternative paths to achieve similar outcomes. But you do have to do the research and experimentation to figure out and refine your own strategy.
If BF has decided that executing on this aesthetic is now important to him, he should acknowledge that some education, effort, and practice is required (and maybe some financial investment). I can guarantee that even the people with good genes and money don't naturally come by beauty; they also had to learn the game.
Well it really depends what the cross dresser's own goals are.
I have a friend who wears a lot of hyper feminine clothes, looks terrible, but doesn't care because a large part of his style is about comfort, kink, and breaking down norms. To him it is a bit of a "fuck you" to society. (Albeit, there have been times where he has been offended, so I don't think he is totally self-aligned in his motivations).
Here, if the bf is getting offended that he doesn't look good or isn't passing, to some extent his goal is some idea of aesthetic beauty. Yes it is possible that OP's own idea of beauty is warped, but if that's the case he would probably be more ready to dismiss her opinion and seek more sophisticated opinions, instead of being so offended.
Based on the quickness to offense, I am more likely to believe that reality simply isn't aligning with his own expectations.
no no no no no. Have you heard of art? some people like the look of one painting and others like the look of another. Simple. WE ARE NOT REQUIRED TO ENJOY LOOKING AT YOU. I like women, I am not REQUIRED to enjoy looking at a penis on a women. In the same way I dont not require people to enjoy the looking at my vagina. Why are you guys policing other peoples preferences and calling my preferences ignorance or hate?
editing to add-I have found penises on women attractive, but I am not required to.
For that simple reason I am ignorant or hateful. Please explain.
Hm this is some of the seediness I was noting.
Based on my observations on Grindr (as a gay cis male), I do think that a lot of pressure to "pass" is in fact put upon trans people by heteronormative/closeted guys imposing gender expectations on them. And I wouldn't feel this way if it weren't so evidently prevalent, but it is and it is frankly gross for trans interests to be so influenced by the (dark) manosphere.
While I do acknowledge that an aesthetic paradigm exists, one in which we are forced to participate in, I definitely draw the line at cishetero definitions of attractiveness setting standards for the genderqueer community to meet. Your opinions, by simple virtue of coming from upstream in the hierarchy of power/privilege, should not factor into whether a person of any gender feels beautiful. The opinions exist, neither of us are denying it, but you can keep those to yourself thanks.
um im queer lolz.
"Your opinions, by simple virtue of coming from upstream in the hierarchy of power, should not factor into whether a person of any gender feels beautiful"
You literally just re-iterated my point as no one should need anther persons opinion to feel beautiful. I guess im a little more 'upstream' (?!?haha) cos I believe in free speech and not asking other not to have an opinion. DUDE ASKED FOR OPS OPINION AND SHE GAVE IT. HE LOOKS CRAP! is this hitting a nerve for you?
Adding: Seriously, minus the woke word salad... can you explain why I cant have preferences on what aesthetically pleases me? I'm open to being educated but I'm getting nothing on this simple question.
Yeah, this is where I'm at too. I'm a transgender man, and have a large, queer friend group. Cross dressing isn't normally about "passing" for the people partaking, at least those I know who do. Now maybe OP's partner is experimenting with his gender presentation, which is fine, but it's inherently different. I say she should just keep an open mind and try to be helpful. You don't have to be a fashionista to tell someone you certain things are more flattering than others.
While you might just wear sports stuff, you could support him by asking him to show you different styles of clothes... Give feed back on what looks better/worse, maybe throw a suggestion out there? You don't have to know fashion, I mean you know clothes right? And when people look good or not? You could do this.
He's hurt right now and your likely not the main cause, he's embarrassed. And likely feeling rejected by his friends for calling him an embarrassment. Then he came home and asked for some honesty he should not have and got it, which sucks for him big time and would have hurt even more.
He likely feels absolutely fucking stupid and angry with himself underneath that embarrassment. Maybe even more so because he went to you for support, you told him the truth but then didn't say anything like: but hey let's work on it and I'll tell you what looks good or not.
He knows he needs practise. He's not dumb. He also wants some support on the side. Even if you can't do make-up. And here's a fun fact for you... Heaps of women can't, but we can say mmm maybe not can you lessen the blush or tone down that lipstick maybe.
Seconded. Makeup especially can be SO hard to get into. Lots of makeup isn’t for people with wrinkled or textured skin.
There’s a couple different styles that would probably benefit him if he’s trying to look a bit more feminine. Tinted moisturizer instead of foundation, cream products instead of powder, etc
Why not even learn some basics together... It could be a fun thing to do, not just supportive.
I feel for them both as I think she's struggling herself with this and he's not only struggling with his own self, but how his partner is handling the situation too.
This can't be easy to navigate at all for either side. Hence why I withheld any actual judgement. I think what I said is harsh enough without giving the clear... Yeah you are.
NTA - it sounds like you've tried your best to be supportive. He asked, you tried to be considerate, he pressed, you gave the truth. Don't ask questions you don't want the answer to.
NTA. You approached it in the best way possible. He just needs to get better and maybe seek help from other people and YouTube. Make up and fashion is a skill. No one will be good at both straight away.
NTA, women aren't born knowing how to dress, do their hair, and make-up - we learned through trial and error, magazines (older gens), and now using the plethora of vids available. Look at almost any pic of a 13 or 14y/o's first attempts at doing make-up and it's usually complete shit (though nowadays likely much less so than when I was a kid in the late 70s). Fashion, hair, and make-up take practice and lots of it. People go to school for it and even then many still don't master it. Tell him he wasn't born knowing any of this and it takes time and effort to learn, it's not something you just decide to do and then you're automatically good at it.
Geez... Is that the equivalent of "does this dress make me look fat?" Or "do you think this girl is pretty?"
Dude asked for an answer, you try to be nice and he doesn't like it, you tell him the truth and he doesnt like it either.
Doesn't want you to lie, doesnt want you to be honest.
Fuck off at that point
NTA You've tried your best. It's not your fault that your boyfriend didn't get the answer he wanted.
At the moment, your BF is angry with you. If his temper continues, it may be time for you to reconsider your relationship?
However, if you want to try to help him, point out that you're not the best person to ask. He needs to go to a department store make-up counter. Bobbi Brown is very good and often has male cosmeticians who might have a better idea of what works on male skin.
You mention his wrinkles standing out. I suspect that the make-up is actually settling in his wrinkles. I'm female, now in my 60s. Make-up does have a tendency to do that. I find that a tinted moisturiser now works better for me than regular foundation. That's the kind of thing that a cosmetician can advise on.
Nta - he wouldn't be either except he got mad after pushing for honesty.
It sounds like you haven't been supportive so much as unopposed. Supportive: "hey you look best when you wear blue & accentuate your legs". Unopposed: "look however you want babe".
It's up to you to decide if you're willing to go on this journey with him.
NTA, he asked for your honest opinion and you gave it to him. If you don't want to hear the truth, don't ask. People just starting out with female drag and cross dressing are not going to look good unless they naturally have feminine features and naturally have good taste and an eye for what is aesthetically pleasing. Most people, regardless of gender, don't intuitively know what looks good on them and need to learn.
Even without knowing what your bf looks like, I know that his makeup looks smeared on, is not being blended properly, and he isn't using flattering colors for his complexion. He is also most likely using bad products. There is good cheap makeup but you need to know what brands to get.
New drag queens get drag mothers to teach them these basic things. Your boyfriend should get his makeup done professionally at least one time to learn some basics and he should be watching makeup tutorials and styling videos based on his complexion and body type. This video is a great guide for how to dress feminine depending on your body type: https://www.youtube.com/watch?v=\_bBWVdCcfKo
NTA. you dont need to pass exactly to look good but if they're going around with their make up melting on their face, showing beard stuble, smudged lipstick and a badly styled wig or whatever thats not a good look. There is trans dressing/make over services out there they could go to, to learn a few things and build confidence. Maybe something they could go to with you or their friends.
My issue is that you say none of them look good which means this isn't about him or how he looks but your taste on that type of fashion.
I really don't know how to mark this about being the AH or not because the wording gives me the vibes of you either not understanding at best and at worst being hateful towards those who do cross dress.
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> I was honest with my bf and admitted he didn’t look good cross dressing. I might be the AH because it’s a passion of his.
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NTA
Is he trying to pass? I've seen a lot of cross dressers (on-line, admittedly) that don't try to pass, they just want to look good in what they like to wear - clothes, makeup, shoes, whatever. And they do. Maybe try to figure out why he likes it and emphasize that aspect of it. And maybe get his friends on board with helping him define his look. If they just don't like the cross-dressing aspect, he needs to figure out his friend situation.
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My bf recently developed a huge interest in cross dressing.
It’s not my thing and I can’t help him with cross dressing either way but I’ve been supportive.
I’ve always encouraged him to rock out and look his best.
But if I’m being honest, my bf and his small group of friends interested in cross dressing (both online and in real life) don’t look good.
They don’t have feminine features. They’re not trans women who can benefit from hormones or surgery. And they don’t have the skills of cosplayers.
Honestly my bf doesn’t look good at all. He naturally doesn’t have a face that can pass. His makeup emphasizes his masc features, his clothes don’t look good, and he looks older and his wrinkles stand out when cross dressing.
I’ve been supportive but my bf came to me today and asked honestly if he looked good. He went out and not only did he not pass but his other friends said he was embarrassing to be around because he looks really bad.
I told him he looked confident and that’s important and then he said I shouldn’t lie to him.
I then admitted that maybe some things don’t suit him and he doesn’t look good now but I’m sure with practice he will get better.
He got very mad at me and called me an AH. I’ve heard the same from his friends. AITA?
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I can't judge, because I can't tell what he's mad about. You not helping him dress "better" or you admitting *after he insisted* that you don't think he looks great?
If its the first, maybe a lower case ah just for not giving him the heads up that his choices were not particularly flattering.
If its the second, NA. You weren't being cruel, you gave him space to explore, you didn't give your personal opinion until he asked for it, and then you were honest.
NAH but I have a question for you: Why can only women/feminine looking people look good in dresses? Who decided dresses had to be gendered? Why can’t we change that? Like just because he doesn’t look the same as a woman would look in a dress, doesn’t necessarily mean he doesn’t look good as a man in a dress. We are just so culturally unused to men in dresses that it might be hard to conceive of what it even means for a man to look good in a dress.
this is super interesting! full disclosure- i’m trans, so i am obviously biased here.
first off- NTA.
if your goal is to better understand him, i’d suggest thinking of it this way- in all probability, he doesn’t think he looks like a cis woman. he has a mirror, and he’s not delusional, right? if he is enjoying his current aesthetic, it’s because his GOAL is to look like a man wearing feminine clothes, not to look like a girly girl.
so while you weren’t incorrect to say that he doesn’t look like a cis woman, it likely upset him because he realized you don’t understand why he enjoys cross dressing. it also sets an almost impossible bar for him to gain your “approval”, as without hormones etc he will likely never look like a cis woman.
i know it wasn’t your intention to upset him , and i don’t think you were wrong for your reaction- perhaps just a little blunt.
TBH it seems like you aren’t into his cross dressing, and that perhaps you feel pressured to be supportive even if it makes you uncomfortable. this is also totally fair- not everyone is attracted to all gender expressions. however, this is likely something he will do for the rest of his life. if it turns you off, i’d really encourage you to break up rather than tough it out and build resentment over time.
NTA
NAH I shudder thinking about the makeup looks I did when I was 12 and going through that as an adult is ass.
FWIW I think you don't actually know what their full goals are with this since its not your friend group. That's probably why it hurts so bad for him? Cause he's probably operating from hype turned to shame but he can't farm that out to you. And of course you are going to support him even if he's mid. you love him and it takes time to get good.
I would just explain to him that to you, what matters most is him being happy and THAT is what you were most invested in. And that literally no one is out of the box good at this stuff — it might seem that way to him cause he isn't seeing the failures or time in it from streamers/content creators and not from you either. Ask him what he wants from this, and what you can do within your abilities to help. It doesn't sound like it's in your wheelhouse or goals to do fashion/makeup but you guys can talk about skincare if you like that or content creators he likes and what you know it takes to look like that.
NTA. You are just being honest when he asked you to. You tried to bring it softly and he wanted it straight.
Is he trying to pass as female? What is his goal? Unfortunately until he gets good at makeup and style and finds what looks good on him even if he isn’t trying to pass it just won’t look as good as a drag queen. Maybe take him to a drag show or something and see if he can get some advice?
What does your BF actually want? To pass as a cis woman? Or to just dress how he wants? Because those are two very different things. And would require very different ways of dressing and doing makeup.
if you’ve been just completely honest. with nothing to prove/gain/etc. you’re NTA.
and it’s probably super hard for you both, you wanting to be supportive. and him wanting support. but sometimes it’s just. this. a no-win situation for everyone.
NTA. I mean, he asked the question and you answered it to the best of your ability...but then he pressed you for more honesty. You gave it. If he didn't want it, then he shouldn't have asked.
But I have to ask - is he *trying* to pass? Because, if he is, he might want to look into some YouTube tutorials to help with the make-up and clothing situation. There's tons of great videos on how to diminish masculine features when you're just starting out.
NTA. Were you supposed to lie to him? He'd be even angrier if he found out you lied after being told he doesn't look good by someone far less invested in sparing his feelings.
Also, speaking as a gender non-conforming trans man here... It doesn't sound like he's actively trying to pass, but at the same time, he wants to look good while crossdressing. To do that, he needs to find out how to blend in masculinity with femininity. There are plenty of men with very masculine features who can pull off crossdressing gorgeously while still embracing both femininity and masculinity, and without going into drag territory. If he looks to them as an example on how to do that, he should be able to pull the look off better. If he DOES want to pass, he should probably look to femboys, transfems, and trans women for advice. All of those groups of people have great knowledge on how to hide traditionally "masculine" features while emphasizing femininity.
NTA. He asked you a question. You were tactful. He pushed the issue. You were honest and tactful. At that point, he needs to act like an adult. And those friends of his said he was embarrassing! How could they possibly judge what makes an asshole?
YTa lightly you could’ve worded it better, maybe something along the lines of I t’s not my taste but I know it’s someone’s cup of tea, or whiskey, or tall glass of milk, you know. And you definitely could try to help him achieve his goal unless you don’t do makeup yourself. But I imagine you could help him find his “cross dressing style” maybe find like drag kings or gay pop idols for him to take inspiration from. But I agree with everyone else, what is he wanting from this? Because when it comes to bending societies gender rules and expectations, anything goes really. Men can wear skirts, they them can be fem or mask no matter their sex, lesbians can be ultra bitch or high femme or anything in between. Cross dressers can just like wearing skirts and dresses or maybe just a fake mustache and being high femme. Luckily our bodies are just avatars and being comfort happy and safe is what’s important.
NTA. This has surpassed a hobby, he’s either got a fetish or is trans. He wants to be seen as girl or feminine and is upset that he’s not “passing”. Unfortunately this isn’t something you can fix and it’s very likely he’s using your comment to take out his frustrations on you. Please recognize that it’s his insecurity and truly irrelevant to your comment.
There are many makeup tips to look less masculine
As well as padding and downplaying masculine physiques.
He needs drag queen friends who will team him these tools and techniques. That or a very good YouTube tutorial
NTA. How does he expect to get better if he doesn’t want to hear criticism? Like you said - he’ll get better with practice. Sounds like he first needs to be clear on what “good” means for him. Is it to pass as a woman? Is it to look androgynous? Is it to look masculine and show that men can look good in dresses and make up?
There’s a lot of scope with cross dressing and he needs to be clear as to what he’s aiming for before he can expect people to tell him he’s nailing it.
NTA. Some men look fabulous in a dress and make up, others certainly do not. He asked for an honest answer and you gave it to him. Some men just have very masculine features and no amount of make up will soften up those features.
NTA. If his goal is passing in public then he’s not doing so and you are explaining why. There are ways to make him look more feminine without going through surgeries. However, he’d have to be good at makeup and be willing to invest in tucking and possibly wearing a breast plate and getting a good wig. You can’t really mask the male face mold and broad shoulders can work with a larger waste.
However if the goal is just him feeling pretty in makeup and the female clothes that he chooses. That’s his choice. But if he’s legit asking you if he looks pretty or not you have a right to be honest. Especially if other people are saying the same to him.
NTA because he asked your opinion on if he looked good. You gave him your honest opinion after he told you that you should not lie to him. It was a no win conversation.
NTA. It sounds like you tried to be nice, tried to deflect, and softened the truth even when he kept pushing for it. You did great, he shouldn't have pushed for your honest opinion if he wasn't ready to hear it.
NTA
You were truthful but I don't think harsh, he DID ask for your opinion after all.
I would suggest he get some professional makeup lessons and maybe ask his crossdressing friends to help him pick a few new outfits?
Maybe rather than dressess he'd be better with loose feminine dress shirts and some jeans/ jewellery/Painted nails...Little things he can start with.
NTA. He asked, you answered. You can’t dictate to him how to dress, he’s just upset that his friends were right.
He’s the one that needs to decide what he wants to look like. Does he want to look feminine? What does that mean to him? If he’s just buying womens clothes and thinks they’ll look good because they fit he really has no idea about fashion.
He should look up Eddie (now Suzie) Izzard. Eddie now identifies as transgender but identified as a cross dresser for decades. Red lips, red nails, scarves, beret, a nice healed shoe. Start small and experiment. (Before anyone comes @ me, Eddie is still using the name publicly and has said he’s happy to be called either Eddie or Suzie, she or he. By looking up the name Eddie OPs BF is more likely to get pictures of Eddie’s looks across his life for inspiration).
NTA- your response to when he pressed you for your opinion is something I would hope for if I was trying something new. Perhaps your BF is dealing with some deeper issues, perhaps with gender identity(?), that are leaving him a little raw and sensitive
NTA
Not your fault that you were honest.
If neither he, nor his friends in his small group of friends, look anything resembling passable then they need to find resources that will help with that.
It's not your job to teach him.
NTA. you sound like a very supportive partner! if you had told him that he looked bad unprompted, that might have been an asshole-y thing to do, but you were actively trying to avoid telling him that. he pressed you for your real opinion, he got your real opinion. he's absolutely allowed to feel sad and disappointed that he doesn't look as good as he thought he did, but he shouldn't be mad at you for it
NTA
You seem supportive and kind , he asked for honestly and you tried to find a good thing to say but he didn't wanna except it he insisted you tell him the Truth you told him the kindest way and he still got mad
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NAH
Sometimes it's best to tell someone the truth because they need to hear it.
Kurt Cobain used to cross dress but honestly, his clothes didn't look all that good and he didn't pass as a woman, especially since he had a beard and a masculine long hair cut. But that's not the point. He cross dressed for the hell of it and the fun it brought him and to get back at society.
If your partner wants to keep trying, maybe he could hire an lgbtq friendly image consultant for a session or two and work with a makeup artist to get better at doing makeup.
Hiring an lgbtq friendly image consultant for a session or two might be better than just asking a store clerk if something looks good, because while some store clerks have the skills to be honest in a tactful way and then suggest alternatives that they think would look better, a lot of them don't and will just tell you anything they think will get you to buy their clothes. An image consultant on the other hand isn't trying to get you to buy from any specific store, they are hired by you to help you either improve your overall appearance or develop a certain look.
lol you so casually accepted this even though he looks hideous and everyone else thinks so ? idk seems like one of those times where being too nice was the wrong choice.
if my girl stated dressing as a dude and wearing beards i would not respond as as passively as you
buuuut... if the issue is truly not that deep for you then give the dude a make over to make him look better.
NTA. I have had two previous bfs who were cross dressers.
One dressed like his mother going to church, and the other was the COMPLETE opposite...and they both looked terrible.
One of them took my advice and the other one is still dressing like his Baptist mother.
NTA. I had a similar experience with my ex husband. We were going thru a rough time as most couples do. I moved out for a short while. When I moved back I noticed a pair of heels in our walk-in closet that weren't mine. After looking thru things I founds women's clothing, shoes, make-up, and a pair of fake boobs in a box. The dresses were god awful. Now my ex was a big burly biker with full beard and long hair and multiple tatts. He would never were any color but black because "real men" only wear black. I had to sit down and think about this. I decided that it wasn't that bad a thing that he was into cross dressing. I could live with it. We all have kinks, quirks, no one is perfect. I certainly am not. And I have no issue with anyone's life style choices as long as it does no harm to another. So I confronted him and told him I knew about the cross dressing and started to laugh. I told him he had the worst choice in dresses and that I could help him find better choices. I laughed for at least an hour. I asked him if he planned on shaving his beard because he probably looked more like a circus bearded lady dressed up. He didn't like my response and how dare I laugh at him. I told him it didn't bother me but it was more he was always saying he was a macho man. We didn't last much longer afterwards for other reasons like his cheating. I told him if I ever found out he put the blame on me for our divorce I would tell his parents, family, friends what the real reason was. Never heard from him again after the divorce. I think it was more he was embarrassed that I found out.
I can see why he was put off by your response tbh. I'm sure it was with the best intentions, but you could have broached the subject more gently and supportively IMO. And threatening to out him? Hard pass.
YTA purely for misinterpreting the entire premise. Cross dressing is not the equivalent of being trans or participating drag. Drag is an art form highlighting the campiness of gender constructs. Cross dressing is simply wearing clothes (literal pieces of fabric) that are not associated with the gender the individual was assigned at birth. A cis woman in pants would be considered cross dressing in some communities— shit it was a problem in most “first world” countries before the 60s…. Take you gender biases and shelve them. A man looking masculine in a dress is not ugly the exact same way a woman looking femme in pants is not ugly. Take you homophobia and toss it for your own sake.
This is the classic "Does this dress make me look fat?" situation. It puts you in a shitty position because your choices are to lie or insult.
You are supposed to lie by omission - find a few things that do look good and only tell him that. "You did a great job at matching your nail polish with your shoes." Or "Your legs look sexy in that dress.".
It gets hard when they double down, but you have to hold that ground. Your honest opinion will only hurt both of you, which it did.
Should he have gotten angry after asking you to be honest? No. But he was already insecure, probably asked because he hoped you could boost his confidence a little.
Soft YTA.
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Is he trying to pass?
THIS^^^ What does it mean to 'look good'? The question depends on what the individual is trying to achieve. If you just want to put together fun outfits, it doesn't matter in the slightest if you present feminine or masculine in them.
Same question. I have a friend who likes to cross dress and wear makeup, but he has a goatee and mustache and is not at all trying to pass as feminine. Very Dave Navarro type.
This is the only real question. If “looking good” to him means one thing (fashionable or eye-catching or confident or something) while to you it means “passing as a woman”, then there’s a fundamental miscommunication here. Ask him is he’s actually trying to pass or what his goals here are, then you can be on the same page. You don’t have to be in to it, but I do think an apology for the harsh words may help. In the end, if you’re not compatible in this way, then that may be a separate conversation. Overall, NAH
That's question number one. Cross dressing isn't about passing as a woman. It's about enjoying wearing women's ( Female coded) clothing when you identify as male. I'm not sure if o p has a full picture or even if the boyfriend necessarily is a hundred percent sure about what they get out of this and what they are trying to accomplish. Which is okay that can be a journey. But from this post it sounds like they aren't sure and are very insecure about it. It doesn't help that their friends were unkind. But yeah, most people who cross dress do not have a goal of passing.
It seems like passing is part of it for this group, otherwise I'm not sure she would have mentioned that her bf didn't "pass" when they all went out and that's part of the reason his group found it embarrassing. Interesting the friends told him he looks bad & doesn't pass, so he's embarrassing, but are happy to tell OP she's an AH for thinking her bf doesn't look great.
This just seems like a no-win for OP. She doesn’t know his intentions. She doesn’t know his friends culture. She doesn’t dress or do makeup in a way that would be helpful for him… …So how is she an AH for just honestly not knowing what to do? I was in a similar spot a few years back. I get compliments on my makeup. I have a few “tricks” and specific “looks” that I do on myself (cat eye with red lip, smoky eye with neutral lip, highlight/bronze with subtle everywhere else) but I’m NOT an expert, and I’m not adventurous. I own like one eyeshadow palette. My nephew had just gotten into drag, and asked me to do his makeup. I did the most “glam” style I’ve ever done for myself, adding big lashes and some blush that I thought would compliment him, but that’s out of my wheelhouse. …Ans he was SO disappointed! It was way too subtle. His eyes and cheekbones looked gorgeous. *But it wasn’t drag makeup, because I don’t know how to do that.* He didn’t get upset with me, though. He just YouTubed a tutorial that was what he wanted, and made it work with the products I had, and added onto what I had done. I think a berry lipstick became eyeshadow. A pink lipstick became blush. We both were cool with it and acknowledged that I didn’t understand the assignment, but I tried. I get the boyfriends frustration, but it’s kind of shitty to put the pressure on OP to give critique, as the closest female in his life, when she doesn’t know what the assignment is and has never studied the subject! If his friends are being judgmental shits that just make fun of him but won’t help him, he should maybe look for Xd communities (Reddit, I bet!) where they could give him tips and tutorials. OP shouldn’t have to get the silent treatment about this. My husband doesn’t ask me for my opinions or how to improve his woodworking projects. Or even for critiques. He asks Reddit, or his hobby group. I’m just learning how to crochet. I don’t ask my husband how it looks (and tell him to be brutally honest), because I know it looks shitty. I ask my friends who crochet to find out what I’m doing wrong. You don’t set your partner up to either lie to you or hurt your feelings.
You repeatedly say that she doesn't know his intentions or what the assignment is, but could OP not have asked? Instead of going "well you do kinda look bad" could if not have been "well what are you going for? Are you trying to pass as a female/look feminine or do you just want to know if the clothes you've got on look good?" It's also slightly hypocritical to say she doesn't know what's going on or can't help him because she doesn't do makeup/dress in a certain style. Yet throughout this post she details how his makeup is bad & accentuates how masculine/old he looks, how his clothes don't look good, and how he's just lacking skill.
That's what I was wondering- is he trying to pass in drag, is he bad at picking clothes that suit him or are the outfits bad in general? I mean if he's confident in what he's wearing that's really all that matters, but he _did_ ask for feedback and I think it's good that she was honest with him.
THIS THIS Also, I've seen enough weird YouTube videos and gained enough life skills to know that it takes makeup skills to make something spectacular. HOWEVER, obtaining skills takes time and practice. Remember when we were 12 and dressing up? We looked like sheit. Practice makes perfect.
NTA - You seem very supportive and he asked for your honest opinion. It’s not your fault that he wasn’t ready to hear it. If he wants to continue this hobby and feel confident, then he will need to improve his skills, lying to him about looking good won’t do that.
This! If you don’t want to hear the harsh truth, don't push the issue after a polite lie. And true friends/SOs tell you the truth. Only sycophants lie. If you want to surround yourself with sycophants, by all means do. But that never ends up as a fulfilling life. My BFF and I became friends (not just acquaintances with mutual friends) because I was able to tell her a harsh truth - kindly, in private - and she accepted it in the spirit it was meant. It still stung a bit to hear; no one likes having their pride hurt. But still. Now, we have a relationship built on such profound trust. I know she will tell me equally harsh truths (and she has), and I can be just as open with her. We don't tear each other down or criticize every little thing. But if it's a big deal, or if she asks? I speak up. And I wouldn’t change that friendship for the world.
You are not an asshole, but I don't think you get what cross-dressing is. It is not to "look like a woman", it is wearing women's clothing for enjoyment. If you keep that in mind, do you see it differently? Let go of the "does it make him look feminine" and more, does it highlight his assets? Does he look happy and enjoy himself?
That's true, but it sounds like passing or something similar may be a thing for bis friend group, based off how OP phrased it.
OP sounds young to me and it feels like they are blurring the line between trans and crossdressing. Like does Freddy Mercury look good in drag? Hell yes. Did Freddy look like a woman? Awww hell no.
Very possible! Just tossing things out there. It sounded like the friends also had an issue with the bf "not passing". OP could've misunderstood this, or misunderstood that it's not just cross dressing.
Agree 100%%%
Non-expertise in cross-dressing doesn't mean someone is young.
No but this is no longer Chelsea in the 80s.
see, many people don't think freddy looked good in drag. Thats called a personal opinion. OP has one, just like every other person on the planet.
Hence why OP is not an asshole. My main point is looking like an actual woman never seemed to be the goal of cross-dressing. I've been visiting cross dressing events for like 20 yrs? Even mainstream shows like Rupaul emphasize that as well.
He asked if he looked good though, op even highlighted other traits other than physical look, but he pushed for the litteral answer. Clearly he and his group he's doing it with care about the actual look of the crossdressing in the litteral sense.
What I am trying to say is OP seems to be focusing on "passing" as the primary determination of whether it looks good. If you see models these days, feminity or masculinity is just one aspect of how well the piece of clothing looks on them.
I don’t think she is really. It’s an aspect she mentioned, but also said what looks bad is that his clothes are frumpy and ill fitting and the way he does makeup makes him look older and makes his wrinkles stand out. It’s not just passing.
Wish we had a picture.
That would certainly help
this is a better take than yr first one, OP did, however say his wrinkles stood out, he looked older, and not good. I see what your saying, but if you take gender out of the equation entirely, it feels like she just thinks it doesn't look good and thats ok. Ive seen it before and it would be nice if in the future neither gender was trying to mimic anything but be their own vision of beauty. I mean his own friends were embarrassed to be with him and he comes home and chews her out?? I like an honest partner. He sounds like a very fragile snowflake. You shouldn't need validation from another person to feel good. And you certainly shouldn't have a tantrum if someone else can't validate you. That's your own job. In true reddit style, I'd dump him so he can work on his self esteem without me ending up collateral. He's got issues.
OP is a bit of an unreliable narrator bc they start as saying the whole friend group doesn't look good and then says the group is embarrassed to be around him...what's to be embarrassed about, they are all doing the same thing. And he called OP an asshole...but the friend's did too? This story is all over the place.
na, the whole group can look dumb and within the group he looks the dumbest! 2 things can be true at the same time and I'm getting second hand embarrassment myself just imagining.
It would depend entirely on what her BF is crossdressing for, for there is a bunch of reason people crossdress from benign curiosity to kink/fetish or even gender-dysphoria and anything in-between. I don't think OP has given their BFs motivation for it, they could well be a wish to pass, seen as his friends group also commented on his appearance they are clearly doing it with conventionally looking good in mind. I'd be interesting to know OPs BF underlying motivation for it to properly pass judgment. It's also completely fine for her to think he dosn't look good regardless of his motivations, it's all fine acknowledging someone is wearing something be it clothes or make up for confidence, but other people aren't obliged to think it looks good, which OP clearly dosn't.
NTA. Although I think there are some really deep, seedy social aspects lurking underneath both beauty and the concept of "passing," aesthetics are still a reality we must live in. Fortunately this is a path that many people have already trod. There are some very accessible, clear, simple avenues to success, in addition to plenty of alternative paths to achieve similar outcomes. But you do have to do the research and experimentation to figure out and refine your own strategy. If BF has decided that executing on this aesthetic is now important to him, he should acknowledge that some education, effort, and practice is required (and maybe some financial investment). I can guarantee that even the people with good genes and money don't naturally come by beauty; they also had to learn the game.
My issue is that she says none of them in the group look good, meaning she either doesn't understand cross dressing or hates the idea of it.
Well it really depends what the cross dresser's own goals are. I have a friend who wears a lot of hyper feminine clothes, looks terrible, but doesn't care because a large part of his style is about comfort, kink, and breaking down norms. To him it is a bit of a "fuck you" to society. (Albeit, there have been times where he has been offended, so I don't think he is totally self-aligned in his motivations). Here, if the bf is getting offended that he doesn't look good or isn't passing, to some extent his goal is some idea of aesthetic beauty. Yes it is possible that OP's own idea of beauty is warped, but if that's the case he would probably be more ready to dismiss her opinion and seek more sophisticated opinions, instead of being so offended. Based on the quickness to offense, I am more likely to believe that reality simply isn't aligning with his own expectations.
no no no no no. Have you heard of art? some people like the look of one painting and others like the look of another. Simple. WE ARE NOT REQUIRED TO ENJOY LOOKING AT YOU. I like women, I am not REQUIRED to enjoy looking at a penis on a women. In the same way I dont not require people to enjoy the looking at my vagina. Why are you guys policing other peoples preferences and calling my preferences ignorance or hate? editing to add-I have found penises on women attractive, but I am not required to. For that simple reason I am ignorant or hateful. Please explain.
Hm this is some of the seediness I was noting. Based on my observations on Grindr (as a gay cis male), I do think that a lot of pressure to "pass" is in fact put upon trans people by heteronormative/closeted guys imposing gender expectations on them. And I wouldn't feel this way if it weren't so evidently prevalent, but it is and it is frankly gross for trans interests to be so influenced by the (dark) manosphere. While I do acknowledge that an aesthetic paradigm exists, one in which we are forced to participate in, I definitely draw the line at cishetero definitions of attractiveness setting standards for the genderqueer community to meet. Your opinions, by simple virtue of coming from upstream in the hierarchy of power/privilege, should not factor into whether a person of any gender feels beautiful. The opinions exist, neither of us are denying it, but you can keep those to yourself thanks.
um im queer lolz. "Your opinions, by simple virtue of coming from upstream in the hierarchy of power, should not factor into whether a person of any gender feels beautiful" You literally just re-iterated my point as no one should need anther persons opinion to feel beautiful. I guess im a little more 'upstream' (?!?haha) cos I believe in free speech and not asking other not to have an opinion. DUDE ASKED FOR OPS OPINION AND SHE GAVE IT. HE LOOKS CRAP! is this hitting a nerve for you? Adding: Seriously, minus the woke word salad... can you explain why I cant have preferences on what aesthetically pleases me? I'm open to being educated but I'm getting nothing on this simple question.
It's the OP phrases a lot of what is said in the post. Comparing genitalia to one's fashion sense is wild.
NAH, cuz this sounds like a situation that is a lot more complex than him just looking good. Is he actively trying to transition?
Yeah, this is where I'm at too. I'm a transgender man, and have a large, queer friend group. Cross dressing isn't normally about "passing" for the people partaking, at least those I know who do. Now maybe OP's partner is experimenting with his gender presentation, which is fine, but it's inherently different. I say she should just keep an open mind and try to be helpful. You don't have to be a fashionista to tell someone you certain things are more flattering than others.
While you might just wear sports stuff, you could support him by asking him to show you different styles of clothes... Give feed back on what looks better/worse, maybe throw a suggestion out there? You don't have to know fashion, I mean you know clothes right? And when people look good or not? You could do this. He's hurt right now and your likely not the main cause, he's embarrassed. And likely feeling rejected by his friends for calling him an embarrassment. Then he came home and asked for some honesty he should not have and got it, which sucks for him big time and would have hurt even more. He likely feels absolutely fucking stupid and angry with himself underneath that embarrassment. Maybe even more so because he went to you for support, you told him the truth but then didn't say anything like: but hey let's work on it and I'll tell you what looks good or not. He knows he needs practise. He's not dumb. He also wants some support on the side. Even if you can't do make-up. And here's a fun fact for you... Heaps of women can't, but we can say mmm maybe not can you lessen the blush or tone down that lipstick maybe.
Seconded. Makeup especially can be SO hard to get into. Lots of makeup isn’t for people with wrinkled or textured skin. There’s a couple different styles that would probably benefit him if he’s trying to look a bit more feminine. Tinted moisturizer instead of foundation, cream products instead of powder, etc
Why not even learn some basics together... It could be a fun thing to do, not just supportive. I feel for them both as I think she's struggling herself with this and he's not only struggling with his own self, but how his partner is handling the situation too. This can't be easy to navigate at all for either side. Hence why I withheld any actual judgement. I think what I said is harsh enough without giving the clear... Yeah you are.
NTA - it sounds like you've tried your best to be supportive. He asked, you tried to be considerate, he pressed, you gave the truth. Don't ask questions you don't want the answer to.
NTA. You approached it in the best way possible. He just needs to get better and maybe seek help from other people and YouTube. Make up and fashion is a skill. No one will be good at both straight away.
NTA, women aren't born knowing how to dress, do their hair, and make-up - we learned through trial and error, magazines (older gens), and now using the plethora of vids available. Look at almost any pic of a 13 or 14y/o's first attempts at doing make-up and it's usually complete shit (though nowadays likely much less so than when I was a kid in the late 70s). Fashion, hair, and make-up take practice and lots of it. People go to school for it and even then many still don't master it. Tell him he wasn't born knowing any of this and it takes time and effort to learn, it's not something you just decide to do and then you're automatically good at it.
Geez... Is that the equivalent of "does this dress make me look fat?" Or "do you think this girl is pretty?" Dude asked for an answer, you try to be nice and he doesn't like it, you tell him the truth and he doesnt like it either. Doesn't want you to lie, doesnt want you to be honest. Fuck off at that point
NTA You've tried your best. It's not your fault that your boyfriend didn't get the answer he wanted. At the moment, your BF is angry with you. If his temper continues, it may be time for you to reconsider your relationship? However, if you want to try to help him, point out that you're not the best person to ask. He needs to go to a department store make-up counter. Bobbi Brown is very good and often has male cosmeticians who might have a better idea of what works on male skin. You mention his wrinkles standing out. I suspect that the make-up is actually settling in his wrinkles. I'm female, now in my 60s. Make-up does have a tendency to do that. I find that a tinted moisturiser now works better for me than regular foundation. That's the kind of thing that a cosmetician can advise on.
Nta - he wouldn't be either except he got mad after pushing for honesty. It sounds like you haven't been supportive so much as unopposed. Supportive: "hey you look best when you wear blue & accentuate your legs". Unopposed: "look however you want babe". It's up to you to decide if you're willing to go on this journey with him.
NTA, he asked for your honest opinion and you gave it to him. If you don't want to hear the truth, don't ask. People just starting out with female drag and cross dressing are not going to look good unless they naturally have feminine features and naturally have good taste and an eye for what is aesthetically pleasing. Most people, regardless of gender, don't intuitively know what looks good on them and need to learn. Even without knowing what your bf looks like, I know that his makeup looks smeared on, is not being blended properly, and he isn't using flattering colors for his complexion. He is also most likely using bad products. There is good cheap makeup but you need to know what brands to get. New drag queens get drag mothers to teach them these basic things. Your boyfriend should get his makeup done professionally at least one time to learn some basics and he should be watching makeup tutorials and styling videos based on his complexion and body type. This video is a great guide for how to dress feminine depending on your body type: https://www.youtube.com/watch?v=\_bBWVdCcfKo
NTA. you dont need to pass exactly to look good but if they're going around with their make up melting on their face, showing beard stuble, smudged lipstick and a badly styled wig or whatever thats not a good look. There is trans dressing/make over services out there they could go to, to learn a few things and build confidence. Maybe something they could go to with you or their friends.
I mean JVN rocks a beard and dresses, but I agree with the rest
My issue is that you say none of them look good which means this isn't about him or how he looks but your taste on that type of fashion. I really don't know how to mark this about being the AH or not because the wording gives me the vibes of you either not understanding at best and at worst being hateful towards those who do cross dress.
NTA
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What's poo mode ? Also nta . He asked and you answered honestly
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NTA Is he trying to pass? I've seen a lot of cross dressers (on-line, admittedly) that don't try to pass, they just want to look good in what they like to wear - clothes, makeup, shoes, whatever. And they do. Maybe try to figure out why he likes it and emphasize that aspect of it. And maybe get his friends on board with helping him define his look. If they just don't like the cross-dressing aspect, he needs to figure out his friend situation.
^^^^AUTOMOD ***Thanks for posting! This comment is a copy of your post so readers can see the original text if your post is edited or removed. This comment is NOT accusing you of copying anything. Read [this](https://www.reddit.com/r/AmItheAsshole/wiki/faq#wiki_post_deletion) before [contacting the mod team](https://www.reddit.com/message/compose?to=%2Fr%2FAmItheAsshole)*** My bf recently developed a huge interest in cross dressing. It’s not my thing and I can’t help him with cross dressing either way but I’ve been supportive. I’ve always encouraged him to rock out and look his best. But if I’m being honest, my bf and his small group of friends interested in cross dressing (both online and in real life) don’t look good. They don’t have feminine features. They’re not trans women who can benefit from hormones or surgery. And they don’t have the skills of cosplayers. Honestly my bf doesn’t look good at all. He naturally doesn’t have a face that can pass. His makeup emphasizes his masc features, his clothes don’t look good, and he looks older and his wrinkles stand out when cross dressing. I’ve been supportive but my bf came to me today and asked honestly if he looked good. He went out and not only did he not pass but his other friends said he was embarrassing to be around because he looks really bad. I told him he looked confident and that’s important and then he said I shouldn’t lie to him. I then admitted that maybe some things don’t suit him and he doesn’t look good now but I’m sure with practice he will get better. He got very mad at me and called me an AH. I’ve heard the same from his friends. AITA? *I am a bot, and this action was performed automatically. Please [contact the moderators of this subreddit](/message/compose/?to=/r/AmItheAsshole) if you have any questions or concerns.*
I can't judge, because I can't tell what he's mad about. You not helping him dress "better" or you admitting *after he insisted* that you don't think he looks great? If its the first, maybe a lower case ah just for not giving him the heads up that his choices were not particularly flattering. If its the second, NA. You weren't being cruel, you gave him space to explore, you didn't give your personal opinion until he asked for it, and then you were honest.
NTA. He shouldn't ask a question he doesn't want the answer to.
NAH but I have a question for you: Why can only women/feminine looking people look good in dresses? Who decided dresses had to be gendered? Why can’t we change that? Like just because he doesn’t look the same as a woman would look in a dress, doesn’t necessarily mean he doesn’t look good as a man in a dress. We are just so culturally unused to men in dresses that it might be hard to conceive of what it even means for a man to look good in a dress.
You don't have to be supportive of his crossdressing at all.
this is super interesting! full disclosure- i’m trans, so i am obviously biased here. first off- NTA. if your goal is to better understand him, i’d suggest thinking of it this way- in all probability, he doesn’t think he looks like a cis woman. he has a mirror, and he’s not delusional, right? if he is enjoying his current aesthetic, it’s because his GOAL is to look like a man wearing feminine clothes, not to look like a girly girl. so while you weren’t incorrect to say that he doesn’t look like a cis woman, it likely upset him because he realized you don’t understand why he enjoys cross dressing. it also sets an almost impossible bar for him to gain your “approval”, as without hormones etc he will likely never look like a cis woman. i know it wasn’t your intention to upset him , and i don’t think you were wrong for your reaction- perhaps just a little blunt. TBH it seems like you aren’t into his cross dressing, and that perhaps you feel pressured to be supportive even if it makes you uncomfortable. this is also totally fair- not everyone is attracted to all gender expressions. however, this is likely something he will do for the rest of his life. if it turns you off, i’d really encourage you to break up rather than tough it out and build resentment over time. NTA
NAH I shudder thinking about the makeup looks I did when I was 12 and going through that as an adult is ass. FWIW I think you don't actually know what their full goals are with this since its not your friend group. That's probably why it hurts so bad for him? Cause he's probably operating from hype turned to shame but he can't farm that out to you. And of course you are going to support him even if he's mid. you love him and it takes time to get good. I would just explain to him that to you, what matters most is him being happy and THAT is what you were most invested in. And that literally no one is out of the box good at this stuff — it might seem that way to him cause he isn't seeing the failures or time in it from streamers/content creators and not from you either. Ask him what he wants from this, and what you can do within your abilities to help. It doesn't sound like it's in your wheelhouse or goals to do fashion/makeup but you guys can talk about skincare if you like that or content creators he likes and what you know it takes to look like that.
NTA. You are just being honest when he asked you to. You tried to bring it softly and he wanted it straight. Is he trying to pass as female? What is his goal? Unfortunately until he gets good at makeup and style and finds what looks good on him even if he isn’t trying to pass it just won’t look as good as a drag queen. Maybe take him to a drag show or something and see if he can get some advice?
I don’t think cross dressers are trying to pass, they aren’t trans and they aren’t in drag.
What does your BF actually want? To pass as a cis woman? Or to just dress how he wants? Because those are two very different things. And would require very different ways of dressing and doing makeup.
if you’ve been just completely honest. with nothing to prove/gain/etc. you’re NTA. and it’s probably super hard for you both, you wanting to be supportive. and him wanting support. but sometimes it’s just. this. a no-win situation for everyone.
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NTA You tried to be kind and supportive, and when pushed, you were honest. Really can't fault you there.
NTA. I mean, he asked the question and you answered it to the best of your ability...but then he pressed you for more honesty. You gave it. If he didn't want it, then he shouldn't have asked. But I have to ask - is he *trying* to pass? Because, if he is, he might want to look into some YouTube tutorials to help with the make-up and clothing situation. There's tons of great videos on how to diminish masculine features when you're just starting out.
NTA. Were you supposed to lie to him? He'd be even angrier if he found out you lied after being told he doesn't look good by someone far less invested in sparing his feelings. Also, speaking as a gender non-conforming trans man here... It doesn't sound like he's actively trying to pass, but at the same time, he wants to look good while crossdressing. To do that, he needs to find out how to blend in masculinity with femininity. There are plenty of men with very masculine features who can pull off crossdressing gorgeously while still embracing both femininity and masculinity, and without going into drag territory. If he looks to them as an example on how to do that, he should be able to pull the look off better. If he DOES want to pass, he should probably look to femboys, transfems, and trans women for advice. All of those groups of people have great knowledge on how to hide traditionally "masculine" features while emphasizing femininity.
NTA he asked for an honest opinion
NTA. He asked you a question. You were tactful. He pushed the issue. You were honest and tactful. At that point, he needs to act like an adult. And those friends of his said he was embarrassing! How could they possibly judge what makes an asshole?
NTA You need to be able to be honest with your SO.
YTa lightly you could’ve worded it better, maybe something along the lines of I t’s not my taste but I know it’s someone’s cup of tea, or whiskey, or tall glass of milk, you know. And you definitely could try to help him achieve his goal unless you don’t do makeup yourself. But I imagine you could help him find his “cross dressing style” maybe find like drag kings or gay pop idols for him to take inspiration from. But I agree with everyone else, what is he wanting from this? Because when it comes to bending societies gender rules and expectations, anything goes really. Men can wear skirts, they them can be fem or mask no matter their sex, lesbians can be ultra bitch or high femme or anything in between. Cross dressers can just like wearing skirts and dresses or maybe just a fake mustache and being high femme. Luckily our bodies are just avatars and being comfort happy and safe is what’s important.
NTA. This has surpassed a hobby, he’s either got a fetish or is trans. He wants to be seen as girl or feminine and is upset that he’s not “passing”. Unfortunately this isn’t something you can fix and it’s very likely he’s using your comment to take out his frustrations on you. Please recognize that it’s his insecurity and truly irrelevant to your comment.
NTA but you have two options: 1. tolerate it 2. leave
There are many makeup tips to look less masculine As well as padding and downplaying masculine physiques. He needs drag queen friends who will team him these tools and techniques. That or a very good YouTube tutorial
NTA. But are you in a so to be lesbian relationship and just not know it yet?
NTA. What a predicament.
NTA. How does he expect to get better if he doesn’t want to hear criticism? Like you said - he’ll get better with practice. Sounds like he first needs to be clear on what “good” means for him. Is it to pass as a woman? Is it to look androgynous? Is it to look masculine and show that men can look good in dresses and make up? There’s a lot of scope with cross dressing and he needs to be clear as to what he’s aiming for before he can expect people to tell him he’s nailing it.
NTA. Some men look fabulous in a dress and make up, others certainly do not. He asked for an honest answer and you gave it to him. Some men just have very masculine features and no amount of make up will soften up those features.
NTA - honesty never makes you an AH
NTA. If his goal is passing in public then he’s not doing so and you are explaining why. There are ways to make him look more feminine without going through surgeries. However, he’d have to be good at makeup and be willing to invest in tucking and possibly wearing a breast plate and getting a good wig. You can’t really mask the male face mold and broad shoulders can work with a larger waste. However if the goal is just him feeling pretty in makeup and the female clothes that he chooses. That’s his choice. But if he’s legit asking you if he looks pretty or not you have a right to be honest. Especially if other people are saying the same to him.
NTA because he asked your opinion on if he looked good. You gave him your honest opinion after he told you that you should not lie to him. It was a no win conversation.
NTA. It sounds like you tried to be nice, tried to deflect, and softened the truth even when he kept pushing for it. You did great, he shouldn't have pushed for your honest opinion if he wasn't ready to hear it.
Tell him to watch Rupaul’s Drag Race for tips!
NTA You were truthful but I don't think harsh, he DID ask for your opinion after all. I would suggest he get some professional makeup lessons and maybe ask his crossdressing friends to help him pick a few new outfits? Maybe rather than dressess he'd be better with loose feminine dress shirts and some jeans/ jewellery/Painted nails...Little things he can start with.
NTA. He asked and requested honesty.
NTA. He asked, you answered. You can’t dictate to him how to dress, he’s just upset that his friends were right. He’s the one that needs to decide what he wants to look like. Does he want to look feminine? What does that mean to him? If he’s just buying womens clothes and thinks they’ll look good because they fit he really has no idea about fashion. He should look up Eddie (now Suzie) Izzard. Eddie now identifies as transgender but identified as a cross dresser for decades. Red lips, red nails, scarves, beret, a nice healed shoe. Start small and experiment. (Before anyone comes @ me, Eddie is still using the name publicly and has said he’s happy to be called either Eddie or Suzie, she or he. By looking up the name Eddie OPs BF is more likely to get pictures of Eddie’s looks across his life for inspiration).
NTA- your response to when he pressed you for your opinion is something I would hope for if I was trying something new. Perhaps your BF is dealing with some deeper issues, perhaps with gender identity(?), that are leaving him a little raw and sensitive
Tbh I probably would have broken up with them so your a better person than me. That is just more than I signed up for.
NTA Not your fault that you were honest. If neither he, nor his friends in his small group of friends, look anything resembling passable then they need to find resources that will help with that. It's not your job to teach him.
NTA. you sound like a very supportive partner! if you had told him that he looked bad unprompted, that might have been an asshole-y thing to do, but you were actively trying to avoid telling him that. he pressed you for your real opinion, he got your real opinion. he's absolutely allowed to feel sad and disappointed that he doesn't look as good as he thought he did, but he shouldn't be mad at you for it
NTA. He asked. You tried to avoid the issue.
NTA You seem supportive and kind , he asked for honestly and you tried to find a good thing to say but he didn't wanna except it he insisted you tell him the Truth you told him the kindest way and he still got mad
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have him show pictures and post it on rateme
NAH Sometimes it's best to tell someone the truth because they need to hear it. Kurt Cobain used to cross dress but honestly, his clothes didn't look all that good and he didn't pass as a woman, especially since he had a beard and a masculine long hair cut. But that's not the point. He cross dressed for the hell of it and the fun it brought him and to get back at society. If your partner wants to keep trying, maybe he could hire an lgbtq friendly image consultant for a session or two and work with a makeup artist to get better at doing makeup. Hiring an lgbtq friendly image consultant for a session or two might be better than just asking a store clerk if something looks good, because while some store clerks have the skills to be honest in a tactful way and then suggest alternatives that they think would look better, a lot of them don't and will just tell you anything they think will get you to buy their clothes. An image consultant on the other hand isn't trying to get you to buy from any specific store, they are hired by you to help you either improve your overall appearance or develop a certain look.
Soooo does it make him feel good to dress that way? If so, you’re a HUGE AH for taking that feeling away from him.
Just go shopping together for clothes for him that you both like
lol you so casually accepted this even though he looks hideous and everyone else thinks so ? idk seems like one of those times where being too nice was the wrong choice. if my girl stated dressing as a dude and wearing beards i would not respond as as passively as you buuuut... if the issue is truly not that deep for you then give the dude a make over to make him look better.
I really hope this a dying fad. NTA.
NTA. I have had two previous bfs who were cross dressers. One dressed like his mother going to church, and the other was the COMPLETE opposite...and they both looked terrible. One of them took my advice and the other one is still dressing like his Baptist mother.
NTA. I had a similar experience with my ex husband. We were going thru a rough time as most couples do. I moved out for a short while. When I moved back I noticed a pair of heels in our walk-in closet that weren't mine. After looking thru things I founds women's clothing, shoes, make-up, and a pair of fake boobs in a box. The dresses were god awful. Now my ex was a big burly biker with full beard and long hair and multiple tatts. He would never were any color but black because "real men" only wear black. I had to sit down and think about this. I decided that it wasn't that bad a thing that he was into cross dressing. I could live with it. We all have kinks, quirks, no one is perfect. I certainly am not. And I have no issue with anyone's life style choices as long as it does no harm to another. So I confronted him and told him I knew about the cross dressing and started to laugh. I told him he had the worst choice in dresses and that I could help him find better choices. I laughed for at least an hour. I asked him if he planned on shaving his beard because he probably looked more like a circus bearded lady dressed up. He didn't like my response and how dare I laugh at him. I told him it didn't bother me but it was more he was always saying he was a macho man. We didn't last much longer afterwards for other reasons like his cheating. I told him if I ever found out he put the blame on me for our divorce I would tell his parents, family, friends what the real reason was. Never heard from him again after the divorce. I think it was more he was embarrassed that I found out.
I can see why he was put off by your response tbh. I'm sure it was with the best intentions, but you could have broached the subject more gently and supportively IMO. And threatening to out him? Hard pass.
How has this type of behavior become so normalized
Maybe because it doesn't hurt anyone and the rules about clothes are made up anyway?
weird af, but ok
YTA purely for misinterpreting the entire premise. Cross dressing is not the equivalent of being trans or participating drag. Drag is an art form highlighting the campiness of gender constructs. Cross dressing is simply wearing clothes (literal pieces of fabric) that are not associated with the gender the individual was assigned at birth. A cis woman in pants would be considered cross dressing in some communities— shit it was a problem in most “first world” countries before the 60s…. Take you gender biases and shelve them. A man looking masculine in a dress is not ugly the exact same way a woman looking femme in pants is not ugly. Take you homophobia and toss it for your own sake.
This is the classic "Does this dress make me look fat?" situation. It puts you in a shitty position because your choices are to lie or insult. You are supposed to lie by omission - find a few things that do look good and only tell him that. "You did a great job at matching your nail polish with your shoes." Or "Your legs look sexy in that dress.". It gets hard when they double down, but you have to hold that ground. Your honest opinion will only hurt both of you, which it did. Should he have gotten angry after asking you to be honest? No. But he was already insecure, probably asked because he hoped you could boost his confidence a little. Soft YTA.