Table for One, Please: Being Single at a Couple’s Resort

I really wish I would have fucked hotter people, I said.

The question was, “What is your biggest regret in life so far?”

I admit that my response was brash, but then again I was sitting in a bikini on the edge of an infinity pool in Mexico, sipping on my third “organic” pina colada, alongside 14 other tourists who had signed up for this Happiness Bonfire.

Our facilitator, Britney, was wearing a flowy embroidered dress that seemed authentically indigenous but that I’d seen on sale at Anthropologie three months ago. She was waving a beaded feather and whispering, “Ignore your censor,” to the circle. “This is a safe space,” she’d said.

But as soon as I finished sharing, she took in a sharp breath and started to wiggle her upper body as if to shake out the exhale. Moments later, she was able to recenter herself, remember the script, plaster on half a smile and say, “Thank you for sharing your truth,” before bowing her head in gratitude. It occurred to me that Britney seemed like the type of person who believed both in crystals and crystal meth.

As the sharing continued, I couldn’t help but reflect on my single status, considering that I had booked a last-minute, two-week trip to an All Inclusive Couples Resort.

I’d rationalized that I would have more fun by myself than if my ex-boyfriend had found his passport in time to join me. Which was typical of him; he really did require outside assistance to do pretty much anything.

I thought about how I described my ex to my friends. “Well he’s taller than me, he’s got a trust fund, he went to Northwestern and he just bought a house.”

It was a sentence I would deliver in the same tone I’d use to order toppings on a pizza. In response, my friends would ask the question they always asked: “But, do you like him?”

Did they not hear? I said trust fund and taller than me. My boyfriends were never hot. Very accomplished, yes. Toes-curling bangable, not so much.

I don’t think I date men who are unattractive because of my own poor self-image. I mean, I grew up without being allowed to watch TV or read women’s magazines. The side effects of which: really high self-esteem.

Men who are hot and successful make me uncomfortable. One, there is just a level of personal upkeep I can’t maintain. And two, I don’t think I could handle all of the competition from women who can and will.

A less unattractive dude will cherish you more. Unattractive is my comfort zone. It’s like the fuzzy sweater that is so warm and soft, you overlook all the holes and stains. I’m ashamed to say that for me, the stranger, the plainer, the better. Like the award-winning poet who was missing three teeth. Three front teeth. I hadn’t noticed in the smoky dark jazz club, but upon kissing him later, I realized that he had a cavernous mouth. But I comforted myself with the fact that he was award-winning and his voice rumbled like James Earl Jones.

Or the child actor who looked like he had the body of a 4’9 kid and the face of a very old man. In his defense, he had a beautiful house in Malibu and also played eight instruments. Eight! And yes, I did make an exception on the height, and I also chose to overlook that he was a black Republican, who was working on a rap song about “self-reliance.”

It’s not my fault you’re sleeping in your mother’s living room.

If you want to get out, you better swish swish on that fast food broom.

I started to suspect I had a problem when I discovered that I was using Tinder wrong. The whole point of the app is to swipe on the hot faces of the people you want to rub body parts with. But when I look at Tinder, I turn into Sherlock Holmes. I spend way too long looking at the background of each photo for any clues to run inventory against the checklist. Holding tigers in Thailand? Adventurous. White guy surrounded by a bunch of brown children in a third world country? Sketchy. Is he leaning on that 7 series because he owns it? Or because he wants me to think he owns it? Is that crown molding in his bathroom selfie pic? Gross at bathroom selfie. Nice about the crown molding.

There was the ring of a gong, signaling that this particular resort activity was now concluded. As I gathered my things I ran into the Surfer. I hadn’t noticed, but he’d joined the circle about 20 minutes before.

I had gotten to know the Surfer over the last few days, primarily because the waitstaff was instructed to sit all the single people together. Team Single consisted of me, the only unattached female, a handful of men in their 40's and 50’s who were recently dumped by their girlfriends/wives, two mother/daughter pairs, and one widower. Most of them were friendly but mainly kept to themselves.

The Surfer, though, he was down for an adventure. Often we would go off together for surf lessons, or to the zoo, or just to wander the street of Puerto Vallarta. Over the last few days, I had seen pictures of his whole family, had debated politics, and if “blue-eyed soul” was really a music genre.

At Happy Hour, like clockwork, the Surfer was seated next to me at the grill. “So beyond figuring out that you need to sex it up with a Latin lover, what else do you have planned for today?”

He said this with a boyish grin.

“You ladies with your checklists.”

“You ladies?”

“Yeah, you ladies, still looking for Mr. Darcy. Have fun. In fact, as a doctor of sorts, I am prescribing you a steamy session with a hottie. Two times a day for the next two weeks.”

He scribbled out a fake prescription note on my wine soaked napkin.

“To be taken orally and . . .”

I snorted.

“Wait, are you a for real doctor?”

“HA! You wish.”

“Is it horrible to want a guy that could be a good provider, who is educated and stable, and can take me on vacations across the world?”

“You mean like the vacation we are currently on?”

“Yeah.”

“So you mean you are willing to date guys you don’t want to hump like a jackrabbit to go on a vacation like the one we are currently on. The vacation you paid for yourself?”

“I don’t get it,” I said plainly.

The Surfer shook his head and laughed.

“You’ve already met a person who is educated and stable and who will take you across the world. He paused, as he saw my eyes narrow.

“It’s you, silly. You’re the man you want to marry.”

He winked at me and chuckled as he grabbed a towel and headed back to the pool.

Later, at dinner, I was seated with Steve, another one of us to-be-pitied singles.

Steve, I was to soon learn, had a mail order bride (his words ,not mine) whose paperwork had been delayed, forcing him to come to Mexico alone. Despite the pending nuptials, Steve leaned in close and informed me that the Surfer had told him I was looking to get frisky with a hot man. He indicated that he was a very dedicated lover and then proceeded to stare me down like Nicholas Cage in a 90's movie.

I should mention that Steve was a very attractive investment banker, so the idea that he chose a mail order bride made me think that I was in the opening scene to a Law and Order episode.

At the same time, I realized I was no better than the mail order bride. For some reason, I was treating the dating process like I was some desperate princess who needed to marry a deformed prince in order to save her sovereign. I was treating sex like a transaction when I really didn’t need to.

The Surfer was right. I already owned my own house and had three degrees. I wasn’t rich, but I did have enough disposable income to drop $1,000 to leash-train my cat. It managed to walk just long enough for an Instagram video, which made it totally worth the investment.

I also didn’t want children, so I didn’t even really need that good DNA. Like, I literally could sleep with whoever I wanted. Crap, I realized.

I’ve spent the last 20 years being some middle-class gold-digger?

Two tables over I heard a man burst out in laughter, and of course, it was the Surfer. He was hunched over his Kindle and trying not to look at the spectacle Steve was creating.

It was then that I noticed something: Surfer was actually quite attractive. Not GQ cover hot, but definitely Macy’s menswear attractive. It also hit me that I had spent my entire vacation with him. We had gotten lost in Yelepa after I mistakenly took us down the wrong path. He’d coached me on how to ride on my boogie board and only laughed at my efforts twice. I had heard about his recent breakups and his guilt over a petty fight with his sister. He knew about my tenuous relationship with my mother, which I shared on a four-hour bus trip into the jungle and he also knew that I don’t eat shellfish, I only take showers at night, and that I don’t sit in the sun.

But most importantly, he had a very broad chest and strong hands. I also liked how he laughed, which was often and easily.

Sure, I didn’t know what he did for work, or where he went to school, and by his own admission he wasn’t even that good of a surfer.

But what I did know for sure was that I had three more nights in Mexico.