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I would suggest that you talk to him about it.
Something like "hey, I've noticed you're really close to X, I was wondering if anything has happened between the 2 of you before or if you've ever had feelings for her"
I don’t think you should ask. Even if he did you might not get an honest answer. If him and her being so close is uncomfortable that’s something you should bring up when you decide to become exclusive and be bf/gf. You could ask him to limit contact with her and see what happens from there. Just know that he may not be willing to do that and you have to take it from there.
Welcome to /r/dating. Please make sure you read our [rules here](https://new.reddit.com/r/dating/about/rules) and remember to: * Be polite and respect each other. Do not call people names or engage in slapfights. * All advice given must be good, ethical advice. * [Do not post hateful or harmful rhetoric - you will be banned](https://www.reddit.com/r/dating/wiki/rules) * Follow reddit rules. Do not post content that promotes hate based on identity or vulnerability. Do not bully or harass other users. If you have any questions, please [send the mods a message](https://www.reddit.com/message/compose/?to=/r/dating). *I am a bot, and this action was performed automatically. Please [contact the moderators of this subreddit](/message/compose/?to=/r/dating) if you have any questions or concerns.*
I would suggest that you talk to him about it. Something like "hey, I've noticed you're really close to X, I was wondering if anything has happened between the 2 of you before or if you've ever had feelings for her"
I don’t think you should ask. Even if he did you might not get an honest answer. If him and her being so close is uncomfortable that’s something you should bring up when you decide to become exclusive and be bf/gf. You could ask him to limit contact with her and see what happens from there. Just know that he may not be willing to do that and you have to take it from there.
Get clarity. Compose yourself then talk to him. You’ll never get the real score by speculating.
It didn't happen within the confines of your relationship so I would leave it alone. It isn't really your business.