I've been friends with this woman for a few years now. She's very attractive and we have similar personalities. I have had feelings for her, but the main reason I have not asked her out on a date is because she has had a boyfriend. I managed to suppress my feelings for the sake of our friendship, and during that time I dated another girl, a relationship that ended last year.
Recently I learned from a close friend of hers that she and her boyfriend of two years had actually broken up a couple of months ago. This was a surprise to me because there had been no signs of their relationship teetering on the edge. At the same time, I never really asked too much about her relationship.
I have found myself once again debating my feelings for her because I don't want to push my luck and have our friendship become awkward. Also, she is just out of a relationship; I don't want to become a potential rebound for her. Plus, we have a lot of mutual friends.
How should I go about figuring out the right time to see if she's ready to start dating again? How do I ask her out as more than friends? We usually work out together once a week and see each other at church on Sundays. Thanks for the advice.
– Stuck Like Glue
Confirm the breakup by asking about it. You want to get the information from the source, and then you can ask how she's doing. She probably won't say much; she didn't even tell you the relationship was over.
My take on long-term friend crushes is that it can be best to get an answer and move on. Yes, it's awkward to tell a friend you have feelings for them only to be rejected. But then the friendship can evolve and become more authentic.
You do not want to tell this woman you have big feelings, only that you'd like to go on a date if she's single and open. Tell her that's all you know about how you feel – that dinner sounds nice. If it's too much for her to think about or she’s not interested, you'll understand. Make that clear.
Of course, you can always go to the mutual friend about this, but again, it's better to ask the person who knows most.
Things could get weird for a bit, even with a simple request for a dinner, but that's life. Sometimes relationships get uncomfortable and routines have to change. Friend groups can survive this kind of thing, and really, you can't guess the timeline on rebounds. She might have been checked out of her relationship for a year. There's no math for this.
Readers? How would you start this conversation?