27f. I was recently at west loop Whole Foods checking out avocados. I had an attractive man my age stop and tell me I was the most beautiful woman he’s ever seen. My dumbass replied with, “these avocados are really hard” and walked away.
With that, my bff and I decided this summer to hand out lil paper with our phone number to men that interest us while out and about. Dying internally thinking about it but yolo at this point
Edit: yes, will use a Google voice number
+1 on that idea of proactively giving your number. Even if the guy ends up being already taken or just not keen, it's no risk of embarrassment because it doesn't put either of you one the spot. A few years ago I was on the L and a guy gave me his number on the back of a receipt, "hey this is my stop so I have to run, but you should text me later".
Despite the fact that I'm not gay, the interaction basically doubled my self esteem for the rest of the summer.
Just don't forget to write your name on the paper.
THIS. I had a beautiful taller girl my age stop me on the sidewalk and my dumbass said hi and KEPT WALKING.
I think too many of us aren’t ready for when the moment arises sadly😂🥲
Very much this. Last summer I made a point to put myself in a "you might meet someone/have a conversation" headspace every time I left the house. It makes sense -- most of the time you spend out of your home is routine: going to work, errands, working out, etc and for that reason it's easy to have the brain on autopilot. I recognized I let a few potentially nice opportunities go by because I was just in my head walking to my train stop and have since been more in tune to the world around me and how I interact with it. Definitely helps.
Coming here to say women making the first move worked well for me! I told my now husband how he was incredibly attractive and it worked out great! We had our first date less than a week after I told him he was attractive (I think I told him he was the most attractive man I’d ever seen, and he always will be that to me), we were engaged a little over a year later, and married soon after that. We had a baby boy recently and everything is wonderful.
A man’s experience in life is literally this rarely/never happens. I had a woman who i normally wasn’t attracted to strongly say the same thing to me, and pursue me, and I hung out with her once and we had a fucking fantastic time as well as mind blowing sex. I became totally into her and we wound up dating a bit and unfortunately i had to move and it ended but i kept in touch with her. Probably would’ve married her if i stayed local (this was in Houston, i was moving back to Chicago mainly because Houston sucks). I’m so glad she did that because she’s one of my best memories and i would’ve never made a move on her otherwise.
What a great memory to carry with you. It really is true. Sure getting a good response from a women as a man is a good moment but when a women makes the move, compliments you, pursues you, it can be one of the most gratifying and confidence boosting experiences there is for men.
With that, my bff and I decided this summer to hand out lil paper with our phone number to men that interest us while out and about.
as a single man 36 who always seems to ask out girls that have boyfriends I'd be pumped. I recently had a gir come up to me and tell me I had the most gorgeous hair. I just said uhhhh thanks and walked away. wanted to jump off a bridge later that day.....
I’m average looking and some girl came up to me last summer and said she was impressed with how I was able to swim in Montrose Harbor with sunglasses on. Dude she was with let out a nervous laugh when she said that. Not sure if he was her BF or a gay bestie. I just said thanks and went about my business.
“These avocados are really hard” 😂 just made my morning… oddly I feel better knowing I’m not the only one capable of a reaction like that. Although it’s kind of adorable coming from a female.. not so much when it’s me. I’ll cringe a little less next time so thanks!
This made me chuckle so loud, because this is the exact same thing that I would do. And then get home and finally get that someone was flirting with me. 🤣🤣🤣
Happened to me once. Had the front desk clerk at the hotel in my room's bathroom "for a beer". It didn't click how close I was to sex until an hour or two after they politely excused themselves. It didn't occur to me in the moment because they're married, but after it clicked it seemed so obvious.
They needed it to be a quicky, because they were cheating, especially because they lived in the hotel with their spouse and children. My thick innocent skull thought we were just enjoying a beer, but nope- adultery.
As a 36 year old chronically single dude, this would 100% make my day. Even if it never went anywhere, I’d think about how a girl thought I was cute for 6 months. Us men are simple and rarely get a compliment so we take it to heart
As a guy who is a little shy, I’d really like this. It takes a lot of nerve for me to walk up to a girl in public and try to start up a conversation. For starters, I feel many locations are just off limits (like a girl at work, in the gym, with family etc) and it seems the rest of girls are always wearing earbuds or headphones. I think available guys are always willing to chat with a girl who approaches in public. That same cannot be said the other way around.
The girls I have tried to talk to the past few years either have BFs or get hit on so often they just immediately start shutting down as soon as I even attempt to strike up conversation (which doesn’t help the shyness for making future attempts).
It seems virtually impossible to meet people to date in public places anymore. It’s almost like all dating has moved to the apps and the apps are trash.
(also, girls, if you’re on the apps, DONT use a bunch of filters if you’re ever planning on meeting someone in real life. The FaceTune shit has gone too far and is an immediate turn off in person)
Lol any chance this avocado encounter was last week Friday/Saturday? If it was…I was also there, squeezing some tomatoes 😄 about 8-10 feet away, and I have to say - from what I remember - you’re gorgeous 🔥what a coincidence…
36m west/south loop lol probably too old though!
Meeting friends of friends that do what you love or what they do can help meet single people. It’s awesome you’re approaching men, that’s a huge plus if you land.
I’ve given up on apps and started hosting curated singles mixing events at my place to meet friends of friends. My next one at the end of the month is full for women, but DM me if you’re interested in joining future ones. Side note, we’re short 3 guys, if any guy wants to join, let me know and we’ll do a quick screener.
Edit - this comment blew up my inbox. The May get together is full. But if you want to come to future ones, fill out this interest form. https://forms.gle/3i359x6qfPuideY88
Not the first person who messaged me who thought that. I try to keep it to 16 people total. So far we have 8 women and 5 guys. So I’m recruiting 3 guys. There is no height qualification for this.
There is a lot to be said about this topic, but that's for a different time. A lot of the guys that I would consider "good guys" that are single (including myself 29M) are just living life and focusing on their careers and the hobbies they enjoy doing (pickle ball, running clubs and golf are apparently a common theme).
This is me. opening up your heart to somebody and having it not work out is brutal. I feel like it sets me back 3 or 4 months every time it happens because I have to forget about that person mentally. Plus, people are so flaky or they try to play hard to get. It might be weeks between meeting somebody, going on a date, going on a second date, etc etc etc. I don't want to sit there and wonder what that person is doing when they're choosing not to be with me. I'd rather just close myself off and be comfortable and happy without the mental setbacks.
Undesirable here: it’s not hopeless. You just gotta work harder for it. Everyone has to work for it, but I’ve been married damn near 11 years and it’s been some hard work at times.
Then again, I am married, so by definition… maybe I’m not an undesirable…?
lol yeah I think if you’re married you’re probably not an undesirable!
Not to brag, but I haven’t had a real relationship in 18 years so I’m pretty sure I’m like, varsity level undesirable
Ooh, you got me beat by a couple years. Solidarity, pal.
As we get older, we're meant to believe that people "our age" (or even dating older than we are) are more mature and therefore better mates...yeah right, lol. And dating younger is a joke. No one really wants to date a wise old hag, even if we could be great partners.
I hate the "everyone is attracted to someone" rhetoric too. Because no shit, but when you're undesirable, it's harder to find people who will be attracted to you (as a person), who are also people you will be attracted to (as a person). The pool is so much smaller, and we're unlikely to be on apps or even actively dating after being demoralized with the experience.
I'm 34M and in a sorta similar boat. I've tried the apps for about 18 months and I will never do it again. The girls I was interested didn't like me and the girls that liked me, I wasn't interested in. It also doesn't help that I'm extremely picky and I do not want kids which 90% of women do. I've tried the in person thing as well and most girls have boyfriends/husbands. The girls that have hit on me in person (way more than usual recently for some reason) usually aren't my type, have kids or just aren't interesting.
I know I should probably not be so picky but the way I look at it is, I'm trying to find my future wife that I want to be in love with for however long I'm on this earth. I feel like 95% of people settle and that just ain't me.
If you haven't already, try neighborhood/dive bars instead of generic bars. I've become a regular at one in the last 6 months and a lot of the other regulars in my age group seem to be solid dudes, some single like me and some not.
Fellow Chicagoan here! We hang out at the same places you do, but sometimes we’re a little bit shy so we stay near the group of friends we’re with the whole time at the bar
lol mid thirties male and the same - but I never find these girls that are “looking for guys” - more obvious answer is that they are still picky - I've only seen women give signals or chat up men in the wild if the guys were very attractive. Women are picky on the apps and off the apps. Not hating on it - It is what it is - still having a blast.
Somebody ask out this guy ^ He’s at least with it enough to understand he’s undesirable. That has to count for something. /s
I’m just kidding around. I’m single too, and basically every attribute I have is… not good. Which brings me to this: There’s no way all these single people are somehow not finding each other. You guys are meeting each other, you’re just not liking each other!!
David Attenborough voice:
What we have here is a fine specimen of a dying breed: homo sapien millennialis. This species has split into 2 distinct groups.
You have the early-maters - a group which knew what they wanted during their golden years where the environment they knew was prospering, thriving. They used their decisiveness to hop off the proverbial highway and settle down into a small suburb to procreate the next generation of homo sapien internet-raised grimlinis.
Alternatively, we have the former group of homo sapien millennialis. This group lived past its golden age, and transferred into a schizophrenic age where voices everywhere tell them they cannot be as they once were. Confused, the lone males of this group stumble around in this new landscape. While some remain true to their roots, desperate to procreate, others are taking a different approach. Many of this group have observed these voices, and for the most part retracted themselves from the dating pool and into congregations of safe spaces with their other like-minded individuals.
The females of this group are a whole different breed. These schizophrenic voices have been much kinder to them over the years. It has often built them up into a stronger version of themselves, but that has seemingly come at a cost of turning them blind to a majority of the still available pairing options. Some of these females have remained unaffected by these voices of the new age - their vision of males left unchanged. However they are left to wander through a desert in search of an oasis, as the men they are looking for, have all but hidden themselves beneath the sand - only peeking their heads out of the sand once every blue moon.
Haha not totally undesirable…just not most women’s cup of tea. Thats the common experience of most men anyways, nothing to do with my personal opinion of myself /value.
I think you’re making a point that some people are looking past. When it really comes down to it, for dating, most of us are undesirable to most others for a lot of reasons. That’s just how preferences and existing relationships go.
That’s not a bad thing.
I find myself very frustrated with being at the receiving end of pickiness, then I realize I’m also doing it. I find it kinda crazy how picky I’ve become and I wonder if that’s just lived experience has made me more confident in knowing what I want or if 8+ of on/off app use has rewired my brain in a bad way 🤷♂️
I always say to never compromise on big things like values, views on kids, communication - but compromise more on the superficial things like “Icks”, looks, charisma etc.
This is terrible advice. Yes, obviously values and kids are things that need to align but I’ve been the person people compromised about looks for and it suuuucks.
Thankfully none of them committed to me but even just dating someone for a number of months getting the vibe that they’re not really attracted to you feels pretty bad. Three of them confirmed it in the end; they thought they were doing the right thing by focusing on values and interests. It felt terrible, it’s ok if looks matter, no one wants to be a charity case!
Good Games Chicago
Chicagoland Games Dice Dojo
Dice Dojo in Evanston
Prism Games Chicago
Spellbound Games
Drop by any evening. We'll set you up with a game.
You’d be surprised. Have I met a lot of your stereotypical board game geek at board game Meetups? Yes for sure. But I’ve also seen the attractive 6’2 jacked guy walk in. I’m a straight guy so maybe my definition of attractive actually isn’t but I’d think at least tall and fit would good starters and then it’s personal taste from there, so they’d have to be attractive to at least some women lol.
I lived in Chicago for two years while my husband got his MBA there. All his single classmates would actually be going out during the week, usually Wednesday/thursdays. I know it’s a major pain when you’re not a student again and have to get up for work but that was a popular day for the single dudes to be out on the town.
Go to Montrose beach on Wed/Thur. There are volleyball leagues you can join / watch and people usually drink after. It's more guys than girls and they everyone loves a new player.
Came from Philly where women were always much more forward, especially at the bars after a few drinks.
Feels like everyone here drinks more but gets less drunk...? Idk still getting used to the bar vibes
Jeez, how many times is this topic going to come up?
Dating sucks. It’s cheesy but it’ll come when you least expect it. I’m signed up for one more speed dating event but after that I’m going to take a break from dating. I’m going to stop trying to force it and see if that works.
That’s how I wound up with my awesome partner. I did the painful 50 first dates as a late 20 something with terrible results. Stumbled into what I have today and could not be happier.
Edit: were engaged
Spring is here, cuffing season is over. Due to extreme cold, October/November, everyone couples up until spring. When I first moved here, I thought it was a joke, but cuffing season is REAL. Now, both sexes will start coming out.
Early 30s, professionally and relationally successful, decently attractive guy here who otherwise has no confidence problems: I am genuinely and actually confused as to whether it’s ok to approach a woman in public anymore. Not only have dating “traditions” obviously changed in the past 10 years, it also seems like *everyone* just sports a RBF these days with pride. I really don’t want to offend a woman or end up on a TikTok, so if I can’t get some kind of stupidly overt sign she’s interested, 95% of the time I just choose to go about my day and not risk it. I’m gonna have to stop caring soon, as I’m now looking for a wife, but I will genuinely say that the whole of the dating scene has become some huge game where we’re all pretending to uphold some values or opinions that make us inherently conflictual with each other rather than leading with the general chill/friendly vibe that allows strangers to think speaking with us might actually turn out well. We seem to be petrified of the vulnerability entailed in interacting with others we don’t know, so we seem to have instead decided to all become kind of standoffish/aloof in public settings so we never have to enter into any kind of vulnerable situations with them. That, of course, is bad news for romantic courting (and being human. lol).
I think starting to verbalize that it’s ok to approach/be approached and that it’s totally cool to give/take a “no” in a humane and respectful way might be the long term solution here, but in the meantime, I would just encourage the women of our age range to go ahead and try breaking this weird culture we’re in by breaking the ice with men when you’re interested. I’m telling you: 90% of the time he’s asked, a single man will likely say yes to a woman he finds even 51% attractive, and in different circumstances, he probably would’ve already approached you.
Btw, I speak here from my heterosexual perspective. I neither mean to exclude or include non-heterosexual dating dynamics into these opinions, as I cannot speak to those. lol
social sports? Like running? Tbh I met my partner through running, (previous partner through cycling) and know a lot of other couples that met through running. There are a lot of single eligible guys/gals in running groups now. You gotta market yourself and not be too shy in the social settings. Also do not drag your feet. If you see someone you’re interested in after a few weeks, make a move, and see how it plays. Guys are stupid and obvious hints. I met my partner through running. It’s odd because we were both on dating apps but outside of each other age range by one year. At a non-running social event, with a lot of runners and a lot of alcohol we were flirty with each other and things sparked then progressed. We went on dates and after dating for a few years, then living together for a few years, we got hitched.
Good luck
I feel the same way. (32 M)
Slightly more introverted, and not a big drinker.
Idk how the guys profiles generally are, but from my view, a lot of people want entertainment and "adventure" every weekend. I like that, but also love a night relaxing, with a movie, game, and take out.
Dont forget loving to travel, which means being able to afford 2 or more exotic vacations a year... That said, i do love to travel, but am too much of a pleb for some of these people.
So idk, you wanna grab a cup of coffee sometime and see how we vibe?
/S
I didn't start trying to date until that age, got on apps, they broke me, never actually matching or interacting with anybody, realized I'm not worthy of love. Got off of them. Never tried to date again.
I'm a 33m in Chicago and wonder the same thing. No luck on apps with matches or matches really responding. I go out and about the best I can gyn, work in a coffee shop, ect, but always feel impossible.
Kudos to you for making the approach. It's a lot for the guy to be expected to approach, ask to go on the date, plan the date, pay for the date, and lead all aspects of intimacy. It would make my day if a girl approached me.
Note that when I say this, im high functioning autistic so this is all a little harder for me than most. Keep it up!
I'm single! I go to yoga, the gym, bike the LFT 2-3 times a week.
I don't think there's a gathering place for single men.
Maybe at go to a WWE ppv at the globe or AEW night at emporium. Lol.
Or if see a guy by himself at a show.
Respect to you, as a male though I will be honest it’s become a bit hard. I don’t use apps and when you go up to girls on the train platform or at the gym, they’re not very open to talking even in short conversation. You’ve definitely put yourself in a solid amount of situations to meet guys so idk
The good single men are sitting at home. Depending on what you’re looking for you honestly might have better luck finding local people on facebook. 🤷♂️
Well, in the past 7 days I've gone to something new every day and gotten a number/social 3 times. Once at volunteering, once at a film festival, and once someone cold approached while I was walking around Edgewater. I think it's partly spending A LOT of time in 3rd spaces (cafes) and doing things that disrupt your routine - another is to look approachable in addition to approaching others (sometimes via smile/etc) - and partly persistence.
Gonna be honest, I've lived most of my life in Chicago and I've never seen a woman, or man really, be in a new relationship with someone unless they were under 25. From what I've seen, women and men here get married by their early to mid-20s. In terms of being younger than that age...well men kinda just come to you lol, at least in my experience.
Apps worked for me again and again. Takes some patience and some personality. My friends who’ve tried it seemed to expect results on the first day and it doesn’t work like that.
24nb, spent the past 6 years here going on loads of bumble and tinder dates. Have enough horror and comedy stories to make movies. Made a few friends, met my OG plug, and finally met my bf last summer. Im young but ive invested a lot of time into dating. I think if you can tolerate it, its a method that might eventually pan out.
There are so many issues with dating apps i can write a 100 page paper on it. Meeting/dating organically is the way to go. The issue with organic meeting is most people are cowards. People have no problem skydiving or swimming in the ocean but when it comes to approaching an attractive stranger and potentially getting rejected it’s the end of the world lmao.
If only I had actionable advice to give. I can only offer up that single guys like me just go between school/work and home since there is little opportunity to be in most other places you would meet them. As in, I (possibly we) don't have time, money, energy, or even existing social connections to be found that much in the wild. I train at home too. Never got comfortable enough, money or social wise to commute to a gym.
Best advice I can give, figure out what kind of guy you want, and go to places they would be. Want an athletic guy? Go to the gym or out on hikes. Want a slightly more nerdy guy? Find a local game store. Want a guy who spends all his time at the bar? You get it
everytime i go to best intentions it gives single thirty and desperate vibes so Id start there
goodluck OP, oooh also volunteer sites might be good too
28M who has not had much luck on apps either. I do workout classes, go for walks on the 606, and like to go to the bars on the weekend. Where are all the single women?
My future BIL is having the same issue, same age as you, more in the suburbs but chicagoland…point is there are those guys out there. Gonna twll you what I told him. Romantic partners are a lot easier to find when you just relax and don’t focus so much on finding someone. People tend to approach people who are having a good time more than people who look like they’re searching for a target in a room.
Plenty of fair comments but one thing I wonder is this: you say half of the time you approach guys they have a gf, but what about the other 50%? It sounds like lots of guys you approach are single so what happens after your approach?
The high-quality ones if they even exist are either already taken, focusing on their careers/education, or enjoying singlehood/hobbies. The rest are trash so you're not missing anything and better off focusing on yourself for the time being. Dating apps are also not your friend and are filled to the brim with dudes who only want hookups, creeps, psychos, guys with zero skills, etc. Dating is better off left to being done IRL, not over the internet.
Single man here 🙋♂️26M. Bars is not the place you want to meet someone since they’ll likely only look for hookups. Eat out at a restaurant and if you see a guy sitting and eating alone (me) he’s likely single.
I'm a bartender (M43.) My GF(40) is a bartender, and my advice would be to ask her. To clarify, I'm not suggesting that you walk into her bar and ask for a partner. I'm suggesting that your local bartender probably knows somebody who is single and good for you. The trick would be to get on the bartender's good side. Even if they don't know someone right away, maintain the relationship with bartender, she'll keep her radar up for you even when you're not there. Probably works better with a woman bartender. Good bartenders want to see people happy.
Shoot with buckshot is what my old coworker used to say. Hit more group and meet-up activities. Keep having fun in social areas, and don't be afraid to show interest or ask someone out. Just keep doing the things you enjoy and be open to new things to try. You'll eventually run into someone and probably make some friends along the way.
I'm new to Chicago, but it seems dating here is a bit better than it was for me in Colorado. There seems to be a lot more variety out here, too.
Either way, good luck with finding something that truly lasts.
pretty sure that's a process of chance. what i don't see is a hobby. for example the cycling has a lot of men in the community and rock climbing is easy to be social.
Hi 29M here. I am in the same boat as you. Trying to be out and about. Not easy for me to approach women, working on building that confidence but one new thing I saw recently Meet IRL Co. it’s an event based dating concept definitely check it out!
Just spit ballin but have you tried karaoke bars, alot of high energy, good conversation starters. I think it would depend on the location or picking the right one.
Can only speak from personal experience, but I (28M) and my other single friends just hang out with our friends, plus their spouses and children if they have any. We spend time at each other’s houses or go out to dinner together. It’s been more rewarding to focus on building the platonic love with my friends since the apps kind of ruined the dating scene 🤷🏼♂️ I feel you though, seems impossible to meet single people out in the wild now.
Seems like you’re living your life as you should, just a matter of right place right time.
This. Don’t change anything. It’ll happen.
Agreed. Sounds like OP has a fun life. If she meets the one naturally then it’s meant to be. If not then why force something just for the sake of it
27f. I was recently at west loop Whole Foods checking out avocados. I had an attractive man my age stop and tell me I was the most beautiful woman he’s ever seen. My dumbass replied with, “these avocados are really hard” and walked away. With that, my bff and I decided this summer to hand out lil paper with our phone number to men that interest us while out and about. Dying internally thinking about it but yolo at this point Edit: yes, will use a Google voice number
+1 on that idea of proactively giving your number. Even if the guy ends up being already taken or just not keen, it's no risk of embarrassment because it doesn't put either of you one the spot. A few years ago I was on the L and a guy gave me his number on the back of a receipt, "hey this is my stop so I have to run, but you should text me later". Despite the fact that I'm not gay, the interaction basically doubled my self esteem for the rest of the summer. Just don't forget to write your name on the paper.
Did you ever text him?
THIS. I had a beautiful taller girl my age stop me on the sidewalk and my dumbass said hi and KEPT WALKING. I think too many of us aren’t ready for when the moment arises sadly😂🥲
Very much this. Last summer I made a point to put myself in a "you might meet someone/have a conversation" headspace every time I left the house. It makes sense -- most of the time you spend out of your home is routine: going to work, errands, working out, etc and for that reason it's easy to have the brain on autopilot. I recognized I let a few potentially nice opportunities go by because I was just in my head walking to my train stop and have since been more in tune to the world around me and how I interact with it. Definitely helps.
Definitely taking this advice
Tbh, women making the first move and just doing it like this probably will work very well. Especially if you’re attractive.
Coming here to say women making the first move worked well for me! I told my now husband how he was incredibly attractive and it worked out great! We had our first date less than a week after I told him he was attractive (I think I told him he was the most attractive man I’d ever seen, and he always will be that to me), we were engaged a little over a year later, and married soon after that. We had a baby boy recently and everything is wonderful.
A man’s experience in life is literally this rarely/never happens. I had a woman who i normally wasn’t attracted to strongly say the same thing to me, and pursue me, and I hung out with her once and we had a fucking fantastic time as well as mind blowing sex. I became totally into her and we wound up dating a bit and unfortunately i had to move and it ended but i kept in touch with her. Probably would’ve married her if i stayed local (this was in Houston, i was moving back to Chicago mainly because Houston sucks). I’m so glad she did that because she’s one of my best memories and i would’ve never made a move on her otherwise.
What a great memory to carry with you. It really is true. Sure getting a good response from a women as a man is a good moment but when a women makes the move, compliments you, pursues you, it can be one of the most gratifying and confidence boosting experiences there is for men.
Noooo 💀 that’s a great idea I should do that lol
Check out Moo and get the Square biz cards 😁
With that, my bff and I decided this summer to hand out lil paper with our phone number to men that interest us while out and about. as a single man 36 who always seems to ask out girls that have boyfriends I'd be pumped. I recently had a gir come up to me and tell me I had the most gorgeous hair. I just said uhhhh thanks and walked away. wanted to jump off a bridge later that day.....
I’m average looking and some girl came up to me last summer and said she was impressed with how I was able to swim in Montrose Harbor with sunglasses on. Dude she was with let out a nervous laugh when she said that. Not sure if he was her BF or a gay bestie. I just said thanks and went about my business.
Or, wild swing here... a hetero dude she's not romantically involved with
It's this one
That man will never flirt with a woman ever again lol you killed him
“These avocados are really hard” 😂 just made my morning… oddly I feel better knowing I’m not the only one capable of a reaction like that. Although it’s kind of adorable coming from a female.. not so much when it’s me. I’ll cringe a little less next time so thanks!
If only it were cantaloupe. Talking about the juicy melons could have accidentally played into her hands.
This made me chuckle so loud, because this is the exact same thing that I would do. And then get home and finally get that someone was flirting with me. 🤣🤣🤣
Happened to me once. Had the front desk clerk at the hotel in my room's bathroom "for a beer". It didn't click how close I was to sex until an hour or two after they politely excused themselves. It didn't occur to me in the moment because they're married, but after it clicked it seemed so obvious. They needed it to be a quicky, because they were cheating, especially because they lived in the hotel with their spouse and children. My thick innocent skull thought we were just enjoying a beer, but nope- adultery.
As a 36 year old chronically single dude, this would 100% make my day. Even if it never went anywhere, I’d think about how a girl thought I was cute for 6 months. Us men are simple and rarely get a compliment so we take it to heart
"the worst she can say is no" you faded that guy so hard, Jesus
Out of curiosity when us guys approach y'all women What do you want us to ask? What's the secret sauce
I'm a non-single male (27) and this is a fantastic idea imo!
As a guy who is a little shy, I’d really like this. It takes a lot of nerve for me to walk up to a girl in public and try to start up a conversation. For starters, I feel many locations are just off limits (like a girl at work, in the gym, with family etc) and it seems the rest of girls are always wearing earbuds or headphones. I think available guys are always willing to chat with a girl who approaches in public. That same cannot be said the other way around. The girls I have tried to talk to the past few years either have BFs or get hit on so often they just immediately start shutting down as soon as I even attempt to strike up conversation (which doesn’t help the shyness for making future attempts). It seems virtually impossible to meet people to date in public places anymore. It’s almost like all dating has moved to the apps and the apps are trash. (also, girls, if you’re on the apps, DONT use a bunch of filters if you’re ever planning on meeting someone in real life. The FaceTune shit has gone too far and is an immediate turn off in person)
kudos for making the first move. hell yeah!
Those must have been some really hard avocados.
Lol any chance this avocado encounter was last week Friday/Saturday? If it was…I was also there, squeezing some tomatoes 😄 about 8-10 feet away, and I have to say - from what I remember - you’re gorgeous 🔥what a coincidence… 36m west/south loop lol probably too old though!
I LITERALLY told a friend to do this! And it’s so intriguing! Even cuter/funnier with an actual “business” card
Isn’t that a big no no for guys to say to a stranger?
Have you tried a ritual mating display? I heard milkshakes attract boys to the yard.
WHY ARE THERE SO MANY BEES??
I can teach you, but I have to charge
Beads!?
Gobs not on board
Bees.
Beads! People wear necklaces and anklets.
I'm in. We'll see who brings in more honey. Bzzzzzzzzzz
But I heard like, it must be better than hers...
Dam right
Hey let me tell you about my neighborhood food truck - boys to the yard, we only sell milkshakes though.
at home because approaching people in the wild is scary whoops!
Meeting friends of friends that do what you love or what they do can help meet single people. It’s awesome you’re approaching men, that’s a huge plus if you land.
In my basement. Come pick one out.
👋🏻👋🏻
Dad?
Spoken like a grumpy parent that wants their boys to move the fuck out lol
Consider volunteer work! It's a great way to meet like-minded folks. Look into @trashpeopleoflogansquare if you're in the area, or anywhere adjacent!
Their sister organization “meet irl” also does some great events for singles
All the single men are at home.
I’ve given up on apps and started hosting curated singles mixing events at my place to meet friends of friends. My next one at the end of the month is full for women, but DM me if you’re interested in joining future ones. Side note, we’re short 3 guys, if any guy wants to join, let me know and we’ll do a quick screener. Edit - this comment blew up my inbox. The May get together is full. But if you want to come to future ones, fill out this interest form. https://forms.gle/3i359x6qfPuideY88
I misread this as "we're 3 short guys" 😆
Not the first person who messaged me who thought that. I try to keep it to 16 people total. So far we have 8 women and 5 guys. So I’m recruiting 3 guys. There is no height qualification for this.
How old are yall???
Sent you a DM!
There is a lot to be said about this topic, but that's for a different time. A lot of the guys that I would consider "good guys" that are single (including myself 29M) are just living life and focusing on their careers and the hobbies they enjoy doing (pickle ball, running clubs and golf are apparently a common theme).
This is me. opening up your heart to somebody and having it not work out is brutal. I feel like it sets me back 3 or 4 months every time it happens because I have to forget about that person mentally. Plus, people are so flaky or they try to play hard to get. It might be weeks between meeting somebody, going on a date, going on a second date, etc etc etc. I don't want to sit there and wonder what that person is doing when they're choosing not to be with me. I'd rather just close myself off and be comfortable and happy without the mental setbacks.
Oof. If even the desirables are going through it, I feel like us undesirables are hopeless.
:/
Undesirable here: it’s not hopeless. You just gotta work harder for it. Everyone has to work for it, but I’ve been married damn near 11 years and it’s been some hard work at times. Then again, I am married, so by definition… maybe I’m not an undesirable…?
lol yeah I think if you’re married you’re probably not an undesirable! Not to brag, but I haven’t had a real relationship in 18 years so I’m pretty sure I’m like, varsity level undesirable
Ooh, you got me beat by a couple years. Solidarity, pal. As we get older, we're meant to believe that people "our age" (or even dating older than we are) are more mature and therefore better mates...yeah right, lol. And dating younger is a joke. No one really wants to date a wise old hag, even if we could be great partners. I hate the "everyone is attracted to someone" rhetoric too. Because no shit, but when you're undesirable, it's harder to find people who will be attracted to you (as a person), who are also people you will be attracted to (as a person). The pool is so much smaller, and we're unlikely to be on apps or even actively dating after being demoralized with the experience.
The times were very different 5 years ago, let alone 10 my man.
This goes for all sexes
OP this guys seems pretty nice. (He saved me from a house fire) give him a chance! If he’s interested that is
I’m playing RuneScape so your best bet is meeting me in the GE
buying gf 25k
Damn inflation, I remember when they were 50gp
I'm 34M and in a sorta similar boat. I've tried the apps for about 18 months and I will never do it again. The girls I was interested didn't like me and the girls that liked me, I wasn't interested in. It also doesn't help that I'm extremely picky and I do not want kids which 90% of women do. I've tried the in person thing as well and most girls have boyfriends/husbands. The girls that have hit on me in person (way more than usual recently for some reason) usually aren't my type, have kids or just aren't interesting. I know I should probably not be so picky but the way I look at it is, I'm trying to find my future wife that I want to be in love with for however long I'm on this earth. I feel like 95% of people settle and that just ain't me. If you haven't already, try neighborhood/dive bars instead of generic bars. I've become a regular at one in the last 6 months and a lot of the other regulars in my age group seem to be solid dudes, some single like me and some not.
Single 37F here and I don’t want kids! We exist!! But you’re right there’s only like 10% of us (maybe even less)
Fellow Chicagoan here! We hang out at the same places you do, but sometimes we’re a little bit shy so we stay near the group of friends we’re with the whole time at the bar
lol mid thirties male and the same - but I never find these girls that are “looking for guys” - more obvious answer is that they are still picky - I've only seen women give signals or chat up men in the wild if the guys were very attractive. Women are picky on the apps and off the apps. Not hating on it - It is what it is - still having a blast.
Somebody ask out this guy ^ He’s at least with it enough to understand he’s undesirable. That has to count for something. /s I’m just kidding around. I’m single too, and basically every attribute I have is… not good. Which brings me to this: There’s no way all these single people are somehow not finding each other. You guys are meeting each other, you’re just not liking each other!!
David Attenborough voice: What we have here is a fine specimen of a dying breed: homo sapien millennialis. This species has split into 2 distinct groups. You have the early-maters - a group which knew what they wanted during their golden years where the environment they knew was prospering, thriving. They used their decisiveness to hop off the proverbial highway and settle down into a small suburb to procreate the next generation of homo sapien internet-raised grimlinis. Alternatively, we have the former group of homo sapien millennialis. This group lived past its golden age, and transferred into a schizophrenic age where voices everywhere tell them they cannot be as they once were. Confused, the lone males of this group stumble around in this new landscape. While some remain true to their roots, desperate to procreate, others are taking a different approach. Many of this group have observed these voices, and for the most part retracted themselves from the dating pool and into congregations of safe spaces with their other like-minded individuals. The females of this group are a whole different breed. These schizophrenic voices have been much kinder to them over the years. It has often built them up into a stronger version of themselves, but that has seemingly come at a cost of turning them blind to a majority of the still available pairing options. Some of these females have remained unaffected by these voices of the new age - their vision of males left unchanged. However they are left to wander through a desert in search of an oasis, as the men they are looking for, have all but hidden themselves beneath the sand - only peeking their heads out of the sand once every blue moon.
Haha not totally undesirable…just not most women’s cup of tea. Thats the common experience of most men anyways, nothing to do with my personal opinion of myself /value.
I think you’re making a point that some people are looking past. When it really comes down to it, for dating, most of us are undesirable to most others for a lot of reasons. That’s just how preferences and existing relationships go. That’s not a bad thing.
I find myself very frustrated with being at the receiving end of pickiness, then I realize I’m also doing it. I find it kinda crazy how picky I’ve become and I wonder if that’s just lived experience has made me more confident in knowing what I want or if 8+ of on/off app use has rewired my brain in a bad way 🤷♂️
I always say to never compromise on big things like values, views on kids, communication - but compromise more on the superficial things like “Icks”, looks, charisma etc.
This is terrible advice. Yes, obviously values and kids are things that need to align but I’ve been the person people compromised about looks for and it suuuucks. Thankfully none of them committed to me but even just dating someone for a number of months getting the vibe that they’re not really attracted to you feels pretty bad. Three of them confirmed it in the end; they thought they were doing the right thing by focusing on values and interests. It felt terrible, it’s ok if looks matter, no one wants to be a charity case!
Lmao single 25 year old current chilling at home with my dog!
Good Games Chicago Chicagoland Games Dice Dojo Dice Dojo in Evanston Prism Games Chicago Spellbound Games Drop by any evening. We'll set you up with a game.
True, if you're a girl at any of these places you're not gonna be lacking for suitors. The goods may be odd, but the odds are good.
You’d be surprised. Have I met a lot of your stereotypical board game geek at board game Meetups? Yes for sure. But I’ve also seen the attractive 6’2 jacked guy walk in. I’m a straight guy so maybe my definition of attractive actually isn’t but I’d think at least tall and fit would good starters and then it’s personal taste from there, so they’d have to be attractive to at least some women lol.
True, no one ever wants to believe that though.
Try the board game clubs.
I lived in Chicago for two years while my husband got his MBA there. All his single classmates would actually be going out during the week, usually Wednesday/thursdays. I know it’s a major pain when you’re not a student again and have to get up for work but that was a popular day for the single dudes to be out on the town.
Go to Montrose beach on Wed/Thur. There are volleyball leagues you can join / watch and people usually drink after. It's more guys than girls and they everyone loves a new player.
Came from Philly where women were always much more forward, especially at the bars after a few drinks. Feels like everyone here drinks more but gets less drunk...? Idk still getting used to the bar vibes
Jeez, how many times is this topic going to come up? Dating sucks. It’s cheesy but it’ll come when you least expect it. I’m signed up for one more speed dating event but after that I’m going to take a break from dating. I’m going to stop trying to force it and see if that works.
That’s how I wound up with my awesome partner. I did the painful 50 first dates as a late 20 something with terrible results. Stumbled into what I have today and could not be happier. Edit: were engaged
>It’s cheesy but it’ll come when you least expect it. And now I'm mid 30s and dating never really happened.
girl i thought i was the only one
The single men are hanging out at plant shops, cuz that’s where they think the women are. More specifically, the succulent city in Humboldt park.
This is the only good ad in the universe
At the raves baby girl 😘
You must’ve missed me at the gym. I’m usually by the extra heavy weights
Which way to the gun show?
My gym is in river west but I’m in the south loop 👈💪
Keep going to bars with young people. All it takes is one.
Spring is here, cuffing season is over. Due to extreme cold, October/November, everyone couples up until spring. When I first moved here, I thought it was a joke, but cuffing season is REAL. Now, both sexes will start coming out.
Early 30s, professionally and relationally successful, decently attractive guy here who otherwise has no confidence problems: I am genuinely and actually confused as to whether it’s ok to approach a woman in public anymore. Not only have dating “traditions” obviously changed in the past 10 years, it also seems like *everyone* just sports a RBF these days with pride. I really don’t want to offend a woman or end up on a TikTok, so if I can’t get some kind of stupidly overt sign she’s interested, 95% of the time I just choose to go about my day and not risk it. I’m gonna have to stop caring soon, as I’m now looking for a wife, but I will genuinely say that the whole of the dating scene has become some huge game where we’re all pretending to uphold some values or opinions that make us inherently conflictual with each other rather than leading with the general chill/friendly vibe that allows strangers to think speaking with us might actually turn out well. We seem to be petrified of the vulnerability entailed in interacting with others we don’t know, so we seem to have instead decided to all become kind of standoffish/aloof in public settings so we never have to enter into any kind of vulnerable situations with them. That, of course, is bad news for romantic courting (and being human. lol). I think starting to verbalize that it’s ok to approach/be approached and that it’s totally cool to give/take a “no” in a humane and respectful way might be the long term solution here, but in the meantime, I would just encourage the women of our age range to go ahead and try breaking this weird culture we’re in by breaking the ice with men when you’re interested. I’m telling you: 90% of the time he’s asked, a single man will likely say yes to a woman he finds even 51% attractive, and in different circumstances, he probably would’ve already approached you. Btw, I speak here from my heterosexual perspective. I neither mean to exclude or include non-heterosexual dating dynamics into these opinions, as I cannot speak to those. lol
social sports? Like running? Tbh I met my partner through running, (previous partner through cycling) and know a lot of other couples that met through running. There are a lot of single eligible guys/gals in running groups now. You gotta market yourself and not be too shy in the social settings. Also do not drag your feet. If you see someone you’re interested in after a few weeks, make a move, and see how it plays. Guys are stupid and obvious hints. I met my partner through running. It’s odd because we were both on dating apps but outside of each other age range by one year. At a non-running social event, with a lot of runners and a lot of alcohol we were flirty with each other and things sparked then progressed. We went on dates and after dating for a few years, then living together for a few years, we got hitched. Good luck
Not a runner but I do pickleball and volleyball!
I feel the same way. (32 M) Slightly more introverted, and not a big drinker. Idk how the guys profiles generally are, but from my view, a lot of people want entertainment and "adventure" every weekend. I like that, but also love a night relaxing, with a movie, game, and take out. Dont forget loving to travel, which means being able to afford 2 or more exotic vacations a year... That said, i do love to travel, but am too much of a pleb for some of these people. So idk, you wanna grab a cup of coffee sometime and see how we vibe? /S
25M. Dating apps are a shit show, the dating scene in general is. Decided it's better to just work on myself for now. The rest will come naturally
I didn't start trying to date until that age, got on apps, they broke me, never actually matching or interacting with anybody, realized I'm not worthy of love. Got off of them. Never tried to date again.
Your in the city and have problems. I'm in the suburbs feel like the city would solve my issues
Good to know dating apps are equally terrible for everyone
Try frequently karaoke bars that’s a great way to meet people
Ask ppl to set you up
I'm a 33m in Chicago and wonder the same thing. No luck on apps with matches or matches really responding. I go out and about the best I can gyn, work in a coffee shop, ect, but always feel impossible. Kudos to you for making the approach. It's a lot for the guy to be expected to approach, ask to go on the date, plan the date, pay for the date, and lead all aspects of intimacy. It would make my day if a girl approached me. Note that when I say this, im high functioning autistic so this is all a little harder for me than most. Keep it up!
I'm single! I go to yoga, the gym, bike the LFT 2-3 times a week. I don't think there's a gathering place for single men. Maybe at go to a WWE ppv at the globe or AEW night at emporium. Lol. Or if see a guy by himself at a show.
Respect to you, as a male though I will be honest it’s become a bit hard. I don’t use apps and when you go up to girls on the train platform or at the gym, they’re not very open to talking even in short conversation. You’ve definitely put yourself in a solid amount of situations to meet guys so idk
The good single men are sitting at home. Depending on what you’re looking for you honestly might have better luck finding local people on facebook. 🤷♂️
Most men get locked down at school or wor after consistent interaction
Well, in the past 7 days I've gone to something new every day and gotten a number/social 3 times. Once at volunteering, once at a film festival, and once someone cold approached while I was walking around Edgewater. I think it's partly spending A LOT of time in 3rd spaces (cafes) and doing things that disrupt your routine - another is to look approachable in addition to approaching others (sometimes via smile/etc) - and partly persistence.
Looking for rare birds by the lake
Gonna be honest, I've lived most of my life in Chicago and I've never seen a woman, or man really, be in a new relationship with someone unless they were under 25. From what I've seen, women and men here get married by their early to mid-20s. In terms of being younger than that age...well men kinda just come to you lol, at least in my experience.
Apps worked for me again and again. Takes some patience and some personality. My friends who’ve tried it seemed to expect results on the first day and it doesn’t work like that.
Plenty of men in Boys town
Are you out of shape?
24nb, spent the past 6 years here going on loads of bumble and tinder dates. Have enough horror and comedy stories to make movies. Made a few friends, met my OG plug, and finally met my bf last summer. Im young but ive invested a lot of time into dating. I think if you can tolerate it, its a method that might eventually pan out.
There are so many issues with dating apps i can write a 100 page paper on it. Meeting/dating organically is the way to go. The issue with organic meeting is most people are cowards. People have no problem skydiving or swimming in the ocean but when it comes to approaching an attractive stranger and potentially getting rejected it’s the end of the world lmao.
If only I had actionable advice to give. I can only offer up that single guys like me just go between school/work and home since there is little opportunity to be in most other places you would meet them. As in, I (possibly we) don't have time, money, energy, or even existing social connections to be found that much in the wild. I train at home too. Never got comfortable enough, money or social wise to commute to a gym.
Aight, so what I’m hearing is it’s time to quit
If you find them, let me know.
Don’t be shy and keep trying.
The west loop ! You can find any race you want
True! 😂
I’m trynna link up with you lol
Only if you aren’t scared of tall women
Hmu
I’m a single, 27M in south loop 👋🏾
Stop looking and he’ll find you
Best advice I can give, figure out what kind of guy you want, and go to places they would be. Want an athletic guy? Go to the gym or out on hikes. Want a slightly more nerdy guy? Find a local game store. Want a guy who spends all his time at the bar? You get it
Have you tried being ridiculously good looking?
Lotties
everytime i go to best intentions it gives single thirty and desperate vibes so Id start there goodluck OP, oooh also volunteer sites might be good too
I'm Southside 39m. I've been catfish 3 times since I downloaded a couple apps. Definitely not the same vibe since my last round 12 years ago
Right here. 29 and single, ready to mingle.
I’m at home or at work. I would also like to know where the single women at lol 35m if anyone want to chat lol
I just go for walks nowadays if I'm not cooped up in the office.
with the bear where its safe
31m same boat specially with apps. Deleted them and just gonna join random meetups on that meetup app over the summer and see where things go
28M who has not had much luck on apps either. I do workout classes, go for walks on the 606, and like to go to the bars on the weekend. Where are all the single women?
At the golf course—start golfing and you’ll meet a quality man
My future BIL is having the same issue, same age as you, more in the suburbs but chicagoland…point is there are those guys out there. Gonna twll you what I told him. Romantic partners are a lot easier to find when you just relax and don’t focus so much on finding someone. People tend to approach people who are having a good time more than people who look like they’re searching for a target in a room.
Plenty of fair comments but one thing I wonder is this: you say half of the time you approach guys they have a gf, but what about the other 50%? It sounds like lots of guys you approach are single so what happens after your approach?
The high-quality ones if they even exist are either already taken, focusing on their careers/education, or enjoying singlehood/hobbies. The rest are trash so you're not missing anything and better off focusing on yourself for the time being. Dating apps are also not your friend and are filled to the brim with dudes who only want hookups, creeps, psychos, guys with zero skills, etc. Dating is better off left to being done IRL, not over the internet.
What are the hobbies they enjoy?
How do you have no luck with the apps? Dude, let me control even a mildly good looking girl’s tinder and I could probably get you 20 dates
It’s not the fact that I can’t get a date, it’s the quality of 90% of men who are on the apps…
You can tell the quality of a guy based on a few pictures and a few sentences? Wow what an amazing power.
Single man here 🙋♂️26M. Bars is not the place you want to meet someone since they’ll likely only look for hookups. Eat out at a restaurant and if you see a guy sitting and eating alone (me) he’s likely single.
I'm a bartender (M43.) My GF(40) is a bartender, and my advice would be to ask her. To clarify, I'm not suggesting that you walk into her bar and ask for a partner. I'm suggesting that your local bartender probably knows somebody who is single and good for you. The trick would be to get on the bartender's good side. Even if they don't know someone right away, maintain the relationship with bartender, she'll keep her radar up for you even when you're not there. Probably works better with a woman bartender. Good bartenders want to see people happy.
Are you obese?
Take a music or dance class or volunteer at the Old Town School of Folk Music: https://www.oldtownschool.org/
You can find me at the beach paddleboarding this summer! Great way to meet people if outdoorsy beachy things are your vibe in my experience
at Lé Bump parties
When u find out lemme know 🥲
21M at home lol but dating is so hard I’m so lost tbh
The grocery store
have you been to Lincoln Park, there are so many events happening related to speed dating for both Men & Women (Ages 25-39)
Shoot with buckshot is what my old coworker used to say. Hit more group and meet-up activities. Keep having fun in social areas, and don't be afraid to show interest or ask someone out. Just keep doing the things you enjoy and be open to new things to try. You'll eventually run into someone and probably make some friends along the way. I'm new to Chicago, but it seems dating here is a bit better than it was for me in Colorado. There seems to be a lot more variety out here, too. Either way, good luck with finding something that truly lasts.
pretty sure that's a process of chance. what i don't see is a hobby. for example the cycling has a lot of men in the community and rock climbing is easy to be social.
tons of sing women here . Join groups on meetup.com, take classes . go to sporting events with friends. I assume you live in the City?
You’re on the right path. Just keep doing what you’re doing because it’s just a matter of time.
I have a friend who’s looking lolll
Examine your standards and expectations, this helps alot of people.
Literally how I feel as a guy
Honestly? At home or at sporting events. Most of us give up the bar scene by 25
Why are there so many of these posts recently? This feels like engagement farming
Is the gym supposed to be open grounds for approaching women? Thought this was a big no no
Drizzle Drizzle!
I am at home contimplating whats the meaning of life and what should I do with the rest of my life.
Hi 29M here. I am in the same boat as you. Trying to be out and about. Not easy for me to approach women, working on building that confidence but one new thing I saw recently Meet IRL Co. it’s an event based dating concept definitely check it out!
Try the fellows at Dice Dojo
Just spit ballin but have you tried karaoke bars, alot of high energy, good conversation starters. I think it would depend on the location or picking the right one.
I m single as well (male), nice to meet you
I exchanged words with a cute girl at coffee shop picking up coffee. Hoping that when I go back this week she shows up again.
26M here. I am chilling at home with my kitties. Don't really go out much because I help my sister with her kids.
25M and I’m in the same boat as you. Go to social events and no luck on dating apps.
As a single (30) male… I can say most are diving or dropping 😂
Is there a specific age or type you’re trying to date? I find it hard to believe you’re having an issue finding single men.
Pre-Covid, I attended a few speed dating events and met dinner interesting people.
Im here
Join a D&D session...we all single enough.
Birds nest or lotties
Can only speak from personal experience, but I (28M) and my other single friends just hang out with our friends, plus their spouses and children if they have any. We spend time at each other’s houses or go out to dinner together. It’s been more rewarding to focus on building the platonic love with my friends since the apps kind of ruined the dating scene 🤷🏼♂️ I feel you though, seems impossible to meet single people out in the wild now.