Hey Cap, ive got some girl troubles i hope you can help me out with. So a couple years ago i got the pleasure of meeting a girl, me and her would hang out almost daily and we became very close, we were extremely flirtatious and everbody thought we were together. But a few months into our friendship our communication went a little cold and we stopped talking for a little while. I then had a brief relationship with someone, and so did she. Its now a year later and we have been hanging out again and i brought up the courage to ask her out. If i would of done this when we were closest back then it would of been an instant yes i believe. But now she is really hesitant, scared of being hurt, and losing me as someone she can talk to. I want some cold truth here should i keep trying or move on?
I’m so sorry that you seem to have missed the window on this one.
You saying “Hey, I’ve always really liked you and I’m glad that we were able to get back in touch. Do you think we could give dating a shot now that we’re both single?” is brave & cool. There’s absolutely nothing wrong with saying it, and there’s nothing wrong with her hearing something like that from a good friend and needing some time to process and perhaps mentally reframe things a bit before committing one way or another. I think the smart thing for you to do now is to treat anything less than “Hell yes!” as “No, thank you” and give her some space. “I had to ask, I only want you to say yes if you feel 100% great about it, so why don’t you think about it and we’ll talk in a few days/weeks/whenever you like.” Giving her and the whole matter some space will be good self-care and good care for the person you like.
It’s also a good tactic for getting to the heart of the matter. If she does like you back, if she is just sort of processing doubts aloud because she wants to be convinced, I think it’s good for you to bow out while she comes to her own conclusions and refrain from trying to convince her. People don’t forget being asked out by their friends, phones and email work both ways, and if her answer to your question a week from now is “You know what, let’s go for it,” she knows how to find you. You being respectful of her reservations isn’t going to lose you any points if this thing is meant to be, and if it’s not meant to be bowing out gracefully is a way of assigning yourself some grace and coolness points even in the middle of something that feels sucky and awkward.