Office Romance (?)

I’m sure someone out there was curious as to whether or not the girl from my office and I went out Friday night.  Unfortunately, I’m starting off this post with bad news: we didn’t.  To be fair,  I think she was exhausted.  She worked very hard throughout the week and probably needed last night to head to bed nice and early.

Around three o’clock on Friday, I noticed she had set up her laptop at a table near my desk in the office.  She was there for a good hour.  I wonder, maybe she picked that spot because she was hoping I’d drop by and say ‘hi?’  Or maybe I’m reading into signals that aren’t there.  The fact is, I didn’t drop by or say anything.  I’m not sure how to act around her during those rare moments when we intersect at the office.  Do I act professional and just say ‘hi’ and continue walking?  Do I start up a conversation?  I have no idea what’s appropriate.  I also have no idea what she wants.

The fact of the matter is, we’ve “gone out” twice, and both times it was more of an organic date that happened out of circumstance rather than someone asking someone else out.  As I pointed to in my last entry, I really like this girl.  She’s smart, passionate and gorgeous.  But both times we’ve hooked up, albeit briefly, she had been drinking.  Maybe she views those times as mistakes?

The past two Fridays, when I seemed to have missed my shot to hang out with her after work (last Friday she already had plans and this Friday she went home before I could catch her to head to bed early), I sent her a message: let me know if you want to grab a drink or a bite over the weekend.  Neither time has she followed up.  Granted, usually I prefer to try to suggest something more specific, but, again, I’m not really sure what she wants or expects — maybe she doesn’t like me that way?

Then again, she has instigated things on the rare occasion.  For example, the second time we hooked up, she leaned in for the kiss that time — the first time I had.  On Tuesday night this week, she g-chatted me out of the blue seemingly just to say hi.  Granted, she might do that to a lot of co-workers.  I don’t know.  Maybe this isn’t really an office romance at all, maybe this is two drunken hookups and my own confusion about whether or not she’s sending signals.

So how do I work this out?  I don’t think there’s a definite answer.  After I missed my chance on Friday night, I spent the night brainstorming a path forward.  I think the plan is going to be this: unless she seems to want to hang out this coming Friday after work, I’ll suggest a more specific Saturday night date — rather than my typical casual, “let me know if you want to get a bite or a drink this weekend.”  I’m thinking of saying something more along the lines of “I was going to try to cook dinner at my apartment on Saturday night, any interest in coming over as an official taster?”  I’m a decent cook and I think romance is nearly unavoidable when you cook a dinner for two.  If she doesn’t seem interested, I might just ask her point blank: “do you want me to stop trying to ask you out every weekend?” — I think I can say it playfully enough that it won’t seem frustrated or bitter, but I just don’t want to spend my time dwelling on her if she’s not interested in.

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