Guy's Guy™
Guys' Guy's Guides™

Sex with Your Ex: The Agony and The Ex-tasy

We’ve all been there. You look down at your phone and you see her face and number. You exhale and answer the call. A few hours later you’re drinking wine with her at an outdoor table near Gramercy Park. Two glasses of Chardonnay later you’re both hungry so you hit the Mexican joint nearby that you two used to enjoy. This time the enchiladas were not a flavorful as you recalled. 

An hour later the sun has gone down and you’re back at your crib. You stare at yourself in the bathroom mirror, wondering if this is a good idea. Then you shrug and return to the bedroom where she’s stretched out naked on your bed with the sheet barely draped around her torso. An hour later it’s all over and she’s fastening her bra and then pulling her hair back. Then, she’s gone and you’re staring at ESPN. Victory….or defeat. You decide.

That’s pretty much how it goes when you hook up with your ex. The motivation could be anything from you missed each other, you’re both horny, you want revenge or closure, you just enjoy spending time together, or the sex was always mind-blowing so what could wrong with another taste? I don’t have a surefire answer for you, amigo, but I’ve been there more than once and what I was always reminded of was that there was a reason that my ex was just that — my ex.

A Few Examples As Food For Thought…

My live-in relationship ended on a sour note. So she rented an apartment a few blocks up the street from me on the West Side. Out of all the gin joints in the world… Anyway, one thing led to another and soon we were having a bite to eat and then dessert on top of my bed on a regular basis.

I was thinking that this was not so bad. I get the sex and not the headache from an overall unsatisfying relationship, which was no one’s fault but our own. We just did not talk about things, and we did not talk about this either until she cut it off, again. This was because the last time she left my flat she put her blouse on backwards and her new boyfriend busted her. 

The joke was on me, but ultimately to my relief she married the guy and they are living happily ever after. That’s good, but it did not do much for me at the time. But, I did get my rocks off when I was still stinging from the initial break up. Good or bad? Eh, I’d call it a draw.

Drop back ten years in time. My high school sweetheart had unceremoniously dumped me during college. I was hurt because of her callousness in how she handled it. I ran into her about five years later in the city. She was living with three girlfriends from college. I brought my friends along and we all went out on the town until the wee hours. I ended up back at her place in bed… with her. I delighted in having her one more time. But, I was not all that attracted to her at this point and the sex became closure for me. I was officially over her forever. I’m sure she felt the same, but I did get a thrill out of seducing her that one last time. But it was all about ego and self-gratification. I guess that at the time I needed it.

There have been others, but as we get a bit older it gets more complicated. I almost dove back in the sack with an ex about five years ago, but if I did there would be strings attached, so I tiptoed through our meeting and eventually sent her on her way without busting a move. Oh yeah, I wanted to get it on, but I knew that it would lead to discussing the relationship again and by now it was over. She’s beautiful, but I did not feel comfortable “taking” what I could have just for my own short-term jollies. We meant more to one another so it would not have been a cool move.  Someone would have been hurt…I think. But, I could be wrong. Maybe she just wanted to rock it one more time.

But that’s the thing. Going back to your ex for sex is more complicated than it seems. Unless you have a clear understanding about what the expectations are, then you need to be mindful of your feelings and those of your ex partner. No one wants to open up old wounds. But, every situation is different so you never know…

Guy’s Guy of The Week: Chris Brown (and Rihanna for that matter) for braving the intricacies of the Ex-factor.

What has your experience been with sex with your ex? 

Image courtesy of