Okay so I (22M) have a very close friend (20F) that I really enjoy being around. I’d say that I’m definitely falling for this girl, so let me just lay out why I might be stupid here.

This girl and I used to work together, but she left and we kept in touch. We’ve both helped each other through some tough stuff, like her breaking up from a not so serious boyfriend recently in a way that made her feel really bad about herself.

We’ve both been there for each other. We both deal with body image issues and it’s nice to have someone to relate to on it. Over time, we’ve both admitted that we like each other. But she was in the unserious relationship and I thought I wouldn’t do that to someone. I should clarify that by unserious, he just wanted something physical and she wanted a relationship, so eventually they just stopped trying.

But now, every night for the past week we’ve called each other either on the phone or FaceTime for at least an hour a night. I felt comfortable enough to tell her a lot of personal stuff that I haven’t told anyone else. We’ve gone onto some sexual topics, not like “what would you do to me” but like “what kind of things are you into”. There’s definitely some flirting from both sides as well.

At this point you’re probably calling me a dipshit idiot, but I don’t know if it’s too early after her sorta-relationship and I don’t know if it’s too soon to ask her to go out. She’s still a bit upset, but it’s more of the “am I just unlovable” than the “I miss him” kind. It happened around a week and a half ago, and I don’t want to come off as that dude trying to “put her back together” or something. Is it too early to ask her out? Should I give it more time or just say fuck it and seize the day? Thanks in advance for any replies!

Tldr: I don’t know if it’s too soon after a kind-of breakup for me to ask her out. I don’t want to be an asshole and ask while she’s still getting over stuff.

1 comment
  1. Hey! It can definitely be hard to know when to make a move and ask someone out, especially a friend. Even when you know they might like you.

    From what you wrote above, it seems like you and her have a connection and that she would potentially want to date you. The only way to know for sure is to ask her of course.

    You’re clearly a very thoughtful person – you don’t want to take advantage of her emotions or be an asshole. The downside of being thoughtful is that sometimes we overthink. Trust me – fellow thoughtful overthinker here.

    And when you overthink too much, you accidentally become selfish and self-involved. Not because you’re actually selfish, but because you’re spending too much time in your own head and forgetting that the other people in the situation are thinking about it too!

    If there is a connection between you and her, she is thinking about it too. Even if you both feel differently, it’s a two-way street, she’s not just on autopilot. There’s no magical amount of time you can wait, or no magical amount of thinking this through that will make the conversation about your mutual attraction easier or less awkward.

    Also, in this situation, where you’re both close and talking every day, maybe finding out her feelings isn’t a formal “asking out” situation. Maybe it’s something more like “I feel really close to you and I would want this friendship to become romantic, when you’re ready. How do you feel about that?” You can of course put it in your own words.

    I hope this helps! You are clearly a good friend and I hope you both get to talk about each other’s feelings for each other soon.

    Good luck!

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