Why She Slept With You: The Recovering Monogamist

Bi-curious and ready to mingle.

An energetic brunette with blue eyes and an easy demeanor, Jen* is the sort of person you hope to meet while traveling. We met on the road and kept in touch even after our separate adventures took us in separate directions. Recently single, Jen is getting back in touch with her wilder side, seeking out new experiences and new kinds of men. We talked about what it’s like to get back out there and get busy.

You’ve been in a few long relationships. Do you think of yourself as a monogamous person?

Recently, I guess, yeah. I’m not so much a relationship person though.

Do you feel you have some sort of a type at all?

I’m in such a transition phase. I used to love the bad boys with the long hair, skinny jeans. But my recent ex, he was a successful business man, just very, very nice. I would always take the train into Long Island to see him after work because he worked on Long Island. When we went out he was always dressed to the nines and I would be wearing my work scrubs. We looked like the odd couple. I would be wearing scrubs and he would be wearing a suit.

So, you’re transitioning over to different men.

I think it takes getting hurt so many times to realize that you need to be with a guy who has a future. And a lot of the guys that I used to date… they were hot and fun but they had no ambitions. Even the guys that have ambitions sometimes don’t have ambitions in any of the departments we want them to, like they’re all crazy.  

Have you had a disappointing experience?

This one time me and my friend were going to have a threesome with [my tattoo artist]. We were being crazy and he was so nervous between the two of us that he couldn’t get it up. He has these two girls in front of him—come on. He was trying so hard, saying that he was never going to live this up. ‘Guys dream about this and I can’t even get it up.’ And he wasn’t even drunk.

Were you ever able to have a threesome, even though it wasn’t with him?

When I was 18, I did – with my best friend and her boyfriend.

You were a very adventurous young woman.

It’s just that for me, it’s about comfort. Once I’m comfortable I’m down for whatever but it takes a while for that comfort level to set in.

Would you be open to something like that with your next boyfriend?

If I trusted him, yes. If I could trust that afterwards he wouldn’t be keeping in touch with that girl. It’s all about trust and comfort.

How do you plan to find that next guy?

I like shy guys honestly. I tend to be the aggressor. I have a great personality. When I’m sober, I’m such a good girl and I’m really not that flirtatious or anything but once I start drinking. It’s funny what alcohol does.

Lowers you inhibitions. I heard this great saying: “No great story ever starts out with, this one time, I was eating a salad….”

Yeah, pretty much!

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

Photos by Terry-Lee Shield / Getty Images