Confessions of a man sleeping around in his 30s

By Johnny Gaffney

Peach hookah smoke and the thumping bass of Daddy Yankee filled the air. It is 3 a.m. of Seis de Mayo and the utility closet of Mexico 2000 (yes, the Williamsburg bar and restaurant) is proving to a difficult place to sleep. I’d spent the evening running food, making cocktails and telling jokes to customers in broken Spanish. I think they were laughing at me but I can’t be sure. I don’t speak Spanish, but I learned that “Como se dice” is really all you need to get by.

Once the last customers leave, I find a nice booth to curl up in. It’s 5 a.m.

I head out once the sun comes up and bike to work at a senior center. I don’t have another spot to sleep lined up tonight — not that I got much shuteye at Mexico 2000 — but I’m pretty sure I could convince one of the elders to let me crash. Dios mio.

This has been my most challenging sleepover yet and I’m just getting started.

In my unnatural habitat

I embarked on a 31 night sleepover tour after my ex broke up with me. One night at a time, I’m asking patient friends and trusting strangers to let me sleep on their couch (or floor or utility closet) as a sort of penance … a self-discovery journey. In my exit interview, my recently-minted ex emphasized her wariness about moving in together, based on my messiness, inability to cook and general ineptitude regarding basic life skills.

Well, I’ll show her. I am in my 30s and I want to have a family. Don’t think I’m fit to live with? I’ll prove it! I decided to rent out my apartment to a French guy I met on the internet and launch into a 31-night experiment to test my ability to cohabitate with someone new, over and over again. Each sleepover would afford me the opportunity to rise to the occasion. I’d modify my behavior to suit my host and their home, and submit to a performance review in the morning. This could be the skeleton key to becoming the ideal domestic partner. This would be the experience I need for the job I want.

Since May 1 I have installed shelves, washed hairless cats and provided a shoulder to cry on for my hosts. I’ve watched couples bicker, heard couples engage in premarital sex (with performative moaning) and witnessed couples offering each other emotional support. I’ve slept over at a cult leader’s pad, crashed a teenage sleepover party (their mother hosted me) and intruded on a couple’s date night.

By week three I had been moving frantically through these unpredictable and often intimate nights with friends and realized that not one of these “sleepovers” had been sexual (or contained sexual undertones) and I hadn’t missed it one bit. Then I slept over at the home of a woman I used to date.

She didn’t want to hook up.

I was actually … relieved?

All the benefits and none of the work?! You mean I can just lay here, laugh and enjoy your company without providing a good or, ahem, service? It was like a snow day! I realized that a sleepover without sex is far more intimate than sex itself. Maybe that’s why some couples save it for marriage. It’s almost … kinky.

When I began this journey, I assumed that by now I would have amassed a toolbox of skills and hacks to adjust to, and excel in, a wide variety of settings. But the tangible takeaways have been few and far between. I have not uncovered any cheat codes for being the perfect partner.

What does keep coming up is the importance and appreciation of soft skills like “listening” and “being considerate.” My hosts haven’t been impressed by my juggling skills, nor have they gotten especially angry at me for my shortcomings as a handyman.

Irene Siderakis, who has allowed my partner Kareem Rahma and I to host our comedy show at Kellogg’s Diner, offered my most enlightening sleepover yet. Over the course of our Friday night sleepover with Irene and her four teenage sons, I failed as both a Greek sous chef for her, and a worthy XBOX player for her kids, but both Irene and the boys assured me that neither of those things mattered. They told me to continue being myself, showing up and walking through each new door with an open mind and heart.

I have only a handful of sleepovers left until my room will be vacated and I can settle back home. I am physically depleted but emotionally inspired by my hosts and the rare quality time our sleepovers have provided. I also need a long, hot shower.

I am now realizing that I may have used premarital sex and dating as a vehicle to access intimacy when all I needed to do was ask a good friend or tolerant acquaintance for a place to sleep. So, even when the French subletter I met on the internet finally vacates my bed come June 1, I will not stop sleeping around..

In the meantime, cool if I crash tonight ?