This is going to be long and rambling, so I apologize in advance (though I'm mostly writing this for cathartic reasons).
I'm not even sure where to start - maybe with a little background. I've been working with this women for almost five years now (we both started there after college). Now, when she first started working there I thought she was cute and I guess I might have had a little crush on her, but it was nothing to be too concerned about – in fact I thought it would probably be a bad idea to date a coworker.
So over the past few years time passes – I date a couple of people (but nothing serious) and she does the same (I assume). During this time I still find her attractive and still have what I would call a 'small crush.' No big deal. We do some stuff outside of work, but only in a group setting. If she reciprocates the feelings I have toward her, I have no idea. Well, about, I don't know, a year ago I'm starting to find myself increasingly attracted to her. While at work I find that I'm making excuses to talk to her or just be around her. And for the past six months or so (I could just be imagining this) it seems like we started to flirt with each other more.
So a few months ago a famous stand-up comedian is coming to town who I know she likes. I think, 'Great! Perfect opportunity to man up and finally ask her out.' So I buy some tickets a bit later and I... hang on to them. I do nothing for weeks (I bought them quite a bit before the performance). Maybe I convinced myself that it 'wasn't the right time' to ask her to go but for whatever reason I waited to ask her to go. The week of the show comes and still I do nothing (!!!). Then the day of the show comes and, of course, if I'm not to feel foolish and be out of a non-insignificant amount of money then I'll need to ask. Well later in the day I ask what she is doing later... and of course she answers that she is going to see that very same show. OK. My fault. It's not like I should have expected otherwise. I go home, tear up the tickets in frustration, and curse at myself ('****ing coward!'). This was embarrassing and painful to type, but it's true.
So a little time passes and while talking one day she mentions that she hadn't been to the symphony in a while and that she would like to go (in general – not necessarily with me). OK. I swear to myself that I won't mess up this time. I keep my eye out for potential performances and while there was nothing locally that seemed interesting, the next town was having a concert after new year's that looked good. So I ask her if she'd like to go and she says yes. Great! I have no idea how she is perceiving this, but that wasn't the important thing at that moment.
The week of the concert comes around, I suggest we go to dinner beforehand and she agrees. The way I figured it, she probably enjoys my company a little bit or else she wouldn't want to spend the time alone with me – so I chalked this up as a bonus. Anyway the day of the concert comes around and I go to pick her up – she looked amazing. If I were to give a play by play of the evening, it would be unbearably long so I'll skip to some impressions. First off, I have no idea if she even thought she was on a 'date' rather than an 'evening out with a coworker'. I mean if I consider it a date while she does not, is it still a date? No. Anyway, the evening goes pretty well and we each go home. The end. I did go to a movie with her last weekend but again, no signal of any sort one way or the other (that I can discern).
So I guess I'm left with a quandary: what, exactly, do I do? Should I spill my guts and hope she reciprocates (or at least interested enough to try things out)? Keep fumbling along like I've been doing (this only appeals to me as a short term solution)? I'm terribly worried that if I did tell her how I felt, and she rejected me, that things would be, well, uncomfortable to say the least. I feel I am prepared for that scenario, however. In case of the most negative reaction I would probably just finish my masters and start looking for a new job in a new city (I've never been super in love with my job so I wouldn't consider it a huge loss). I'm just very confused on how (or if?) to proceed. It's exhausting to think about and unfortunately it's all I can do. I feel a little better after letting this out and if anyone has any comments, then great. Hopefully some of them might help.
