Your Heart

Confessions Of A Girl Hooking Up With An Engaged Guy

By March 3, 2016 1

I was out one night about a week ago when I met This Guy. He was a friend of a friend,  was very cute and we hit it off immediately. Our banter dripped with sexual tension — balancing flirtatious digs with genuine compliments — and by 2:30 am, we were cozy and hidden away from everyone in a corner-booth tipsily drinking wine and sneaking kisses. It was on.

After what seemed like hours of teasing each other, we decided to go back to my apartment. The 10 block walk took a half-an-hour because every 40 feet we’d stop and make-out in the street. We were completely those people.

If at this point you are thinking, “this is the most perfect meet-cute I’ve ever heard,” then you’d be on my same page.

When we finally got back to my apartment, we had barely made it into the elevator before he had one his strong hands going up and the other going down my dress. He somehow grabbed my keys and pushed us through the opening door without ever taking his hands off of my boobs. 

At this point, I should tell you that I’m no stranger to dating older men. This Guy, who’s 9 years my senior, was just as well dressed and charming as all of the other 30-42 year olds I’ve spent time with over the last few years. But despite having been with honest-to-goodness grown-up men, I had never been with someone I would really call a man — like a, James Bond, Clint Eastwood, Don Draper-type man — a fact I became acutely aware when This Guy sat on the foot of my bed, and extremely slowly, as if he was intimately aware of just how lightly he could brush away the shoulders of my dress to make it slip off, undressed me. 

So now if you’re thinking, “wow, that’s really hot.” then you’d be on my same page. 

After an hour, (AN HOUR!!!!) of fooling around, we moved on to the main event (sex, duh), and he didn’t have a condom. 

“Are you serious?” I asked him, irritated, horny and prettttty drunk, “I don’t have sex without condoms.”

“Yes, Relax,” he responded. “What is this, 1998?” 

Not entirely sure what flashback to his high school sex-ed class he was having, I very drunkenly exclaimed, “You’re right! It’s 2016, and I should be an empowered woman with condoms #beyoncefeminism, but I don’t. So, we won’t. BYEEEE !!!!” And with that I rolled over, still naked, and hoped he got the point to GTFO of my apartment. 

Point taken, he got up, went to the bathroom (which he used it without shutting the door, without flushing, without putting the seat down and without washing his hands) and left. Please keep in mind that less than 20 minutes ago… — Quel nightmare.

If at this point you’re thinking, “Ew, I hate him!” we’re on the same page. 

The next morning, he texted me: “Hey, I’m really sorry I was such an asshole last night…can we blame it on blue balls etc?”

After some thought, I decided that I had been accusatory in my tone when when I asked him about not having a condom, and that I am just as responsible for having a condom as he is. I also realized that while I had orgasmed twice, he hadn’t at all. He may not have been his best self in the moment, but I hadn’t been either, so I forgave him. 

Are we still on the same page?

A few hours later, and looking forward to my next rendezvous with This Guy, I receive a phone call from our mutual friend.  When I told her about what had happened with This Guy, she got a little weird. After a few minutes, she finally told me: HE’S ENGAGED.

If now your heart is a little broken and you’re a angry and confused and cursing yourself for accepting his bullshit apology, we would not be on the same page. 

It sort of surprised me how little emotion I felt upon learning about the relationship status of This Guy. Mainly, I felt bothered and irritated because it added a level of complication to a relationship that I really wanted to be easy. After all, it was the hottest (almost) sex of my life. 

Three days of researching what I should do and how I should feel (which involved texting a Sex and The City-esque cast of friends),  texted him:

“Hey. Friend let me know you have a fiancé. If you want a friend, we can forget Friday night ;)”

He texted back immediately.

“Deal. ;)”.

If at this point you’re thinking “Wow, this girl (me) is a terrible person who should feel terribly about this,” we would, again, not be on the same page.

I’ve been battling a barrage of internal questions for the better part of the past week: Am I a horrible person for hooking up with him to begin with, considering I didn’t know he was engaged? What if I hooked up with him again, now knowing that he’s committed to someone else? What about the fact that I’m trying to keep him in my life as my friend? After all, we clicked on an emotional, physical and intellectual level, and I’m friends with plenty of people I’ve seen naked.

Really, though, (and the Sex and The City cast and I are still trying to figure this part out) — to what extent am I responsible for the things he did to her? And why should I care? I don’t know his fiancee, and all I did was take a hot guy home from the bar and try to have sex with him. What really did I do wrong? 

Because when it comes down to it, I am not responsible for the actions of anyone other than myself. 

But as women, we are raised to feel responsible for others. We feel bad about things that simply aren’t our fault, and guilty for reasons that make absolutely no sense —like me feeling semi-guilty about the fact that some guy cheated on his girlfriend (okay, fiancee) with me. How is that myfault?! 

Awhile back, Pantene launched an incredibly successful campaign, #ShineStrong, connected to its “Sorry, Not Sorry commercial” which pointed out many of the things for which women apologize and shouldn’t. A guy bumps you on the subway and you say sorry, a waiter brings you iced tea when you asked for water; you apologize for preferring water. Women feel and carry the shame, guilt and worry of other people’s actions as if those actions are their own.

Regardless of what the “right” thing to do in this situation is (and let’s be honest — the world is full of complicated grey areas and there’s really no such thing), I’ve spent too much time worrying about what I should or shouldn’t do instead of just doing what I want. But one thing I know for sure: what happens in the next chapter of my relationship with him will not about That Guy, but about This Girl. 

Did we end on the same page?


  • Lisa P.

    Kudos to the article and I recognize that you are trying to be self-empowering. But in actuality, you are engaging in behaviors that directly harm others. So morality is not up for debate. You are making bad choices, you are behaving with cruelty and selfishness, and you are wrong for doing so. You should not be proud.