The Most Embarrassing Sex Story Of My Life

When your job is writing and sharing incredibly personal stories, there’s a question you have to run through in your head a few dozen times a week.

How embarrassing is this story, and is the value in it (be it entertainment, educational, or both) enough that the benefit in sharing it outweighs how mortifying it is?

For me, the initial embarrassment has always been worth it. I’ve made a name for myself sharing a little too much about my personal life, and I’ve never regretted a story I’ve told. These experiences, though embarrassing, often offer a lot of insight into the nature of relationships, hookup culture, and rash decision making.

Also, I mean, they’re just pretty f*cking funny.

However, there’s one story I’ve never told because I couldn’t justify the embarrassment, regardless of what kind of Grey’s Anatomy-style “lesson of the day” it had the potential to teach others. The time has come though, as I’m older and more secure in who I am.

Plus, I just moved halfway across the country, so there’s little chance that any of the parties involved will ever see me again anyway.

So here goes.

There’s a kind of person I’ve always respected in the same way you respect cowboys and world-famous cat burglars—people who just seem to live a lifestyle with an attitude and level of innate skill you could never hope to attain. These are the people I call “Just-Go-With-It Dudes,” those few aloof individuals who dive headfirst into crazy situations without overthinking or panicking.

In late 2013, I was coming off a series of brief pseudo-relationships that had all (to different extents) collapsed as a result of my overwhelming anxiety and need to overthink everything. When I eventually got back into online dating and got a date for the following week, I had a conversation with my best friend (who’s very much a Just-Go-With-It Dude).

“It’s simple,” he told me, “if you’re overthinking everything, do the opposite. 'Yes-Man' it: on this date, just go with the flow and see where it takes you.”

Now, I immediately wanted to tell him how very un-simple this idea was, about all the problems I could run into, and what a minefield that was to navigate—but that felt like overthinking it, so I agreed.


I’m running down a Brooklyn street at 1 AM on a Thursday, drunk off my mind, smelling bad, with no money, holding up a pair of dress pants with a series of water stains in the crotch and thighs. What did I learn from this?


I met Scarlett (that’s what we’ll call her) on Wednesday night at a mostly empty little dive in Williamsburg. There was no way she was taller than 5’2”, and her demure manner immediately made me nervous. I don’t do well with the shy—my 6’5” frame and tendency to over-project when I speak usually makes them scatter like cockroaches when the kitchen light is turned on.

Just go with it, I thought to myself as I ordered my double Jack & Coke.

She shyly ordered a single Jack & Coke and offhandedly joked about me “not getting too drunk” before we sat at our table.

With every round of drinks, I’d loosened up and Scarlett became more… forward. There’s no doubt in my mind that I was drunker than she was—even at a foot taller than her and double her weight, doubles makes for a hell of a drink.

By round two, she told me how cute she thought I was. By round four, she grabbed me by the lapel of my blazer and pulled me in for a kiss. I remember the taste of sh*tty rail whisky as we kissed, unsure if it was my breath or hers (it was both), and looking at her through my drunken, double-visioned eyes as I pulled away.

Both of her were really pretty.

By the end of round seven, she wanted to hook up in the bar bathroom. It had been a while.

Well, is this a good idea? I thought to myself. I’m not entirely sure I can even walk to the bathroom. However, in the spirit of not overthinking, I decided to just go with it. We walked together into the unisex bathroom: a dingy, square room with a stall, urinal, sink and hand dryer. We locked the door behind us and sloppily started making out against the wall of the stall. Eventually, she nudged me down onto the toilet seat and began to kneel down in front of me.

I was compelled to mention how the floor tiles were completely brown with grime, but that felt like overthinking it.

This is going really well, I thought to myself as I closed my eyes and leaned my head back. I should try just going with it more ofte-

In that moment, as though the Universe knew I was starting to mellow out, and decided to dispel some karmic justice, I felt something warm in my lap.

I looked down to see the contents of about 5 single Jack & Cokes in my naked lap.

I heard the sound of the door.

I looked up, and she was gone.

Before any feelings of disgust or revulsion could truly kick in, I remember clearly thinking, Yeah. That’s about right.

I frantically grabbed all of the remaining toilet paper and did my best for the sake of damage control. After quickly running out of paper I stood up, pants still around my ankles, and penguin-waddled over to the sink. I splashed my lap clean, but my thighs and boxers were soaked. There wasn’t any toilet paper left, and there were no paper towels anywhere…

I looked at the hand dryer, installed low into the wall. Defeated, I slowly, penguin-waddled over to it, hit the button, and tried my best to angle my lower body for the warm air to dry myself, so I could end this nightmare.

In the ten seconds that followed, three things happened in succession.

1. I caught a glimpse of myself in the bathroom mirror, and had that moment where you think of every decision you’ve ever made that led you to a moment as low as this one.

2. I realized that when Scarlett bolted out the bathroom, I never locked the door behind her.

3. I heard a noise and looked behind me, and there was a large man standing, arms crossed, in the bathroom’s doorway. And here I was, drunk, with my dick in an XLERATOR hand dryer.

I turned around and looked at the guy, grasping and holding up my pants. For a moment, it looked like the weirdest Old West standoff in history. I ran past him, down the hall and out of the bar, leaving behind my open tab and debit card.

So, this is how my night of “just going with it” ends. I’m running down a Brooklyn street at 1 AM on a Thursday, drunk off my mind, smelling bad, with no money, holding up a pair of dress pants with a series of water stains in the crotch and thighs. What did I learn from this?

You can never really escape who you are. A character on one of my favorite shows once said “the problem with a disguise is that it’s always a self portrait.” Even when we try and escape ourselves, there are certain things we just can’t run away from. When you’re pretending to be someone else, you’re still very much in there.

The experience also taught me to get out of my comfort zone. Don’t get me wrong, it was a complete and total disaster, but up to a point the whole thing was going really well. Plus, once you’ve had someone throw up on your disco stick, things can really only go up from there. In the years since, I’ve made more of a conscious effort to do things that I normally wouldn’t for the sake of the experience. It’s led to a lot of ups and downs, but it’s definitely made me a more confident and adventurous person, and I’m grateful for that.

Sometimes, even if it’s scary and even if it doesn’t end well, you’ve just gotta go with it.

P.S. Eat healthy starches before you drink. It’ll fill you up and help keep your blood sugar stable. Plus, you won’t be able to puke as much. (I did the research after this experience.)

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