This woman I've been friends with for quite a while asked me to be her plus-one to a friend's wedding when her boyfriend had to cancel last minute. The wedding and reception went really well, nothing romantic or scandalous happened between us. My friend confided in me that she brought me because she "needed someone fun, someone who can handle an open bar and who will get along with my friends."
At the end of the night we went our separate ways amicably. Thing is, two weeks later I discover through the grapevine that her boyfriend broke up with her. Before all of this, I used to have a big crush on her, and now that I see a window opening, I want to go for it. I haven't seen her since the wedding (it's been a little over five weeks now), as we've both been busy and on separate vacations. I haven't gotten a good chance to talk with her in person to see how she's feeling, both about the breakup and, potentially, me. I was thinking of getting together with her casually when she gets back into town, all the while pretending I don't know about her breakup so that I could see if she takes the conversation in that direction.
My question is how does one transition from this platonic position to a more romantic/serious one? She's really incredible all around so I really want to get this right. I feel like I already have a huge advantage with her but how do I go about handling this somewhat delicate situation?
The best path is the honest one. It's the one that involves shooting your shot.
Ask her to join you for a meal, and then (during said meal) let her know you had a great time at that wedding. Tell her you feel that way about her, too – that if you had to go to a formal event with friends and cheese plates, she'd be your ideal plus-one. (It's always nice to hear that kind of thing.)
Also tell her you heard about the breakup (I don't see a reason to lie about having that information). Be sensitive and listen to anything she wants to say about that. Then, depending on what she discloses, go ahead and explain that you'd like to take her out on something you could both think of as a date. Nothing huge, no big promises, just more time together – with potential. Make it clear that if it's not something she wants, you'll understand.
It might be too soon for her to pursue any of this, but please let her know the stakes are low right now. You were psyched to be asked to that wedding, and it had everything to do with her. You'd like more time to figure out what that means.
Readers? How should the LW pursue this? Is it too soon or is this the window? Also, what platonic people have you taken to weddings? Was there potential for more?