Why She Slept With You: The Office Dater

Some women don’t mind an ugly man.

Petite with curly brown hair, Kate* works in advertising and moonlights as a writer. I met her at work, where she carried herself with an attractive confidence, and we kept in touch. Single and dating, she told to me about why she’s become more aggressive and why she’s not looking for a pretty man. She wants what she wants and she’s willing to go get it.

Where do you look for men?

I really like dating guys I work with. It’s terrible. I don’t recommend it to anybody but at the same time, it’s this weird attraction because, you know you work together, you spend a lot of time together and at the same time it’s kind of taboo. I remember being tentatively at a work event and I never talked to him in my life but he was Head of Legal, a lawyer and really kind of high up there; so good looking. He had no idea who I was and I saw that he was talking to some girl and I was not having it, for some reason that night: ‘Oh please, he’s not talking to her.’

I walked over to him – my drunk ass –  and said to the girl, “Hi, excuse me, hi, ”to get her out of the way. I said to him, “I have a pressing legal matter that I need to discuss with you urgently.” Long story short, it worked.

Who would have thought a lawyer would fold on legal jargon.

Yeah. We started dating after but we ended up breaking up a few months later.

Is there something that you’re into physically?

I like short guys; not shorter than me but I like a shorter guy. I love good arms…. It doesn’t matter to me, you know. I’ve had sex with some really ugly guys. Like honestly, some really unattractive men. And that’s OK.

There are some really beautiful women that go out with really unattractive men.

If they’re interesting and have a good personality that matters more to me than anything else. Everyone can be attractive in a certain way.

Is there a moment where you realize that a guy is the one that you want to sleep with?

I think if they have a good sense of humor, if they can kind of roll with my weird, dry humor and not be offended or they have to keep up in conversation. I think that a lot of times you talk to a really good looking guy then you realize that he has nothing in his head and it’s the biggest turn off. I don’t want anything to do with you. I think, like a double edged sword, someone can be kind of not be super attractive at first but you talk to them for like 20 minutes and you’re like, ‘Woah.’ He is awesome and that can be super attractive.

And how weird does it get the first time?

The first time you sleep with someone you want it be, not normal, but kind of like a little bit normal. You know, this goes here that goes there, we’re learning things – but don’t try and stick it in my ass the first time we’re sleeping together. Keep it just a little bit normal for a second and then maybe three weeks from now we’ll talk about it. Give me 24 hours to prepare myself and we’ll think about it.

That’s a thing now.

Why do guys love that? I don’t understand.

Can you tell me about a time, maybe when you were out, when you met a guy and let’s say it was a one-night stand – what were the sequence of events that led up to you sleeping with him.

I was out with friends and I saw this guy from across the room and I though he was really cute and I didn’t really know if he would notice me, it was in Williamsburg and I remember he went to the bathroom and it was a co-ed bathroom type thing so I went and stood in line. I went to the bathroom, I’m such a predator, that’s the thing, I won’t sleep with a guy if he’s pursuing me. If it had been the other way around, if he would have pursued me, same situation, at a bar and the guy is good looking and if he would come up to me I would be so turned off. So as I stood at the bathroom, I held the door and he came out and held the door for me and I was like, yes, win. Later on when I kind of was getting near him at the bar, I struck up conversation and it kind of went from there. 

I talked to him and I moved away from him at one point in the night and he came back to me. It was nice to kind of get that reciprocating but in the beginning, I have to be the one that is pursuing someone. Hunting.

Is that the only way that it usually works for you?

Every person that I have seriously been interested in the past three years, I have been the first one to initiate.

*No, that’s not a picture of Kate. That’s a picture of a very lovely woman modeling for a stock photographer.

Photos by Markus Amon / Getty Images