Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

OMG, I Think I Have a Date Tonight With…

OMG, I Think I Have a Date Tonight With... just a story  iStock 000005327644XSmall 271x300Sometime, somewhere in the last few days I heard someone talking about dating a person from .  Or maybe it was something I read.  Anyway, it made me think of this story.

It was the last time I went out with a man from work, although I still cringe when I think of it as “a ”.

It was over a decade ago.  He and I didn’t work closely together.  In fact, days passed when we didn’t see each other. We worked in different departments, worked physically nowhere near each other. The only reason we really knew each other at all was because we were both on the leadership team. So once every two weeks we had to sit in the same dull meetings (which we each managed to find reasons to skip pretty damn frequently).

Anyway, one day he sees me and mentions a play that he’s going to go see. It was off-off broadway. Something I’d heard of and was interested in.  He asked me if I wanted to go with him. But he didn’t ask in a date-y way. It was casual, like he had an extra ticket. I though maybe he belonged to one of the theater clubs, where you can get tickets really cheap or maybe got them from a friend (I sometimes get free tickets from friends who are actors, etc).

And honestly, here is where I sound like a big ole bitch, it didn’t occur to me that he might be asking me out on a date. Sure, we were more or less in the same group.  But I was just so… out of his league. There, I said it. I said yes to the play, thinking it would be cool to get to know him better as a friend, and we talked about grabbing something to eat beforehand.  Again, it all sounded casual to me. Like we were going straight from work and would be hungry so we should eat before the show.

So the day came and he was much more dressed up than usual.  I wasn’t.  And he made sure to drop by my office mid-day to say hello and that he was looking forward to seeing me later. And it hit me.  OMG, I think I have a date tonight with…

OMG, I Think I Have a Date Tonight With... just a story  iStock 000005327644XSmall 271x300I didn’t know what to do.  I didn’t want to go on the date, because I knew it would be awkward and icky. But I couldn’t cancel either.  So I went.  And it was more awkward and icky than I could’ve possibly imagined.

Dinner was painful. I tried to stick to work topics, and he kept on trying to flirt with me.  When the bill came I took out my wallet and offered to pay for the whole thing.  In a friendly, “you got the play, I’ll get dinner” kind a way.  That’s probably exactly what I said.  And he got upset and insisted on paying.

Skip ahead to after the play.  He had a car (in Manhattan, WTF?) and insisted on driving me home, even after I said it really wasn’t necessary. And when we got to my place he leaned over and tried to kiss me. I felt I had no choice but to say the words.  “No, I’m sorry. We’re never going to be more than friends.” Or some variation of that.

And then he asked why. So I politely, but firmly, told him that I had a strict Don’t Shit Where You Eat policy and I could never date a guy from work. At which point he got mad and sad that was a stupid rule and that I was being ridiculous or something like that.  And I quickly got out of his car and avoided him for as long as I could, which was probably no more than a couple of weeks.

Things were never good between us, after that.  Even though I tried hard to not reject him. To make it about the fact that we worked together. I guess he felt embarrassed, or something.

I’m pretty sure there’s no point to this story. I do have a pretty strict Don’t Shit Where You Eat policy.  But I would’ve broken it in a heartbeat if I met someone I really wanted to go out with  (now that I’m self-employed, it kinda doesn’t matter). And I can’t imagine any circumstance under which I would’ve accepted a date with this guy. I was interested in befriending him because that’s the kind of person I am. I tend to make friends at work. Allies.

I guess one of the reasons this date/non-date is something I still remember, after all of these years, is because he was so upset when I pulled away from him in the car.  The fact that I made it about us working together didn’t matter. Since then I’ve tried to be more conscientious about not accepting dates with men who I KNOW I wouldn’t ever want to kiss. Because the look on his face when I pulled away was just so pathetic.  I’d like to avoid seeing that expression ever again.  Or as rarely as possible.


Tags: , ,

11 to “OMG, I Think I Have a Date Tonight With…”


  1. Tahoe Bill says:

    “I’m not into you” is actually a better, healthier response than “I have a don’t date at work rule”. Former is true, latter is not–i.e. you said straight up that you’d break the rule for a different person. Honesty is the key to never seeing that expression again.

  2. Pansophy says:

    Well technically the ‘rule’ proved to be correct. Work was awkard there after.

    • Simone Grant says:

      Absolutely, I was so glad that I could avoid him frequently. Because he was so difficult to be around after that. And I just felt badly about it. As if I’d done something wrong.

  3. Brittany says:

    Not your fault that he misread how you felt. I’m not a confrontational person at all, and generally take the “mature” route by telling him I’m seeing someone else. So I can understand where the no coworkers comment was coming from.

  4. Jeremy says:

    I was most intrigued by your view that he was “so out of your league” — what with your recent discussion of your comparatively (at least among your peers) relaxed view towards “deal-breakers”. Is the concept of “league” different from a “deal breaker”? Who or what defines the league, and does it vary from city to city, with age, etc.? For example, women here in Los Angeles tend to over-value their physical attractiveness, when, in fact, it is so common here as to be essentially meaningless. Thus, their view of what league they are in differs from the perception of an astute man.

    • Simone Grant says:

      That ‘out of his league” comment was a sloppy way of saying what I meant. I don’t really believe in leagues, per se. He was neither attractive, funny, or particularly bright. He was a decent guy. A nice enough person. But there was not a thing about him that I found interesting – that would make me want to date him.

  5. I guess it’s always better to qualify the event as date or non-date beforehand.

    I think, though, in response to what to say when you’re not interested – you can say anything since the point is you aren’t interested, it doesn’t matter why. Some people won’t accept any reason, whether it’s true or not, so I try to go first with what’s honest or second what’s easiest.

    There’s nothing wrong with telling that man you have a work policy, whether it’s the actual reason you don’t want to date him or not.