Sex & the Upper East Side Heads to the Hamptons

My friends were dropping like flies. First went Pookie, engaged to her college beau of seven years. Next came Jenny Saurs, then Annie Smalls. I was one of the few left standing in my close-knit group of Upper East Side friends, still searching for that uptown prince. Who would have thought that a handsome, witty, intellectual, non-chain-smoking, employed man with a functioning air conditioner and a similar affinity for all things vodka and Law & Order was so much to ask for in a city of eight million people?

Instead, my past six years of drinking, dating, and dwelling in a jaded city that never sleeps had left me with men who still relied on their mothers to make their lunches and do their laundry; men who thought the answers to their woe-is-me sad state of life’s affairs was at the bottom of a bottle whiskey and a carton of Marlboro Lights; and men who thought it was acceptable to lie and cheat their way through a relationship. Sure there had been a pseudo-African prince, a LeBron James look-a-like, and a few unforgettably sexy cab rides in there, but those sure as hell hadn’t landed me in a stable, secure relationship accessorized with a diamond ring.

So what better way to forget the John Does of the past than with a girls’ weekend in the Hamptons? I’d spent a summer in the Hamptons years past with my first New York summer love, The Captain. It was before the days of Gossip Girl and The Real Housewives of New York, where my only impression, before stepping off that green Jitney was an episode of Sex & the City where Samantha had picked up a bad case of crabs. Luckily, rather than a creepy STD, The Captain showed me a whole new world, Aladdin-Jasmine style, complete with sunset yacht rides, Vueve, and oysters on the half shell. So here I was, years later, with my best gals, my stars and stripes bikini, and a few penis straws just to get us in the bachelorette spirit.

Emily and I were the only singletons on our girls getaway/bachelorette party/happy engagement weekend, with Emily in her usual verge-of-blackout, don’t-be-shocked-if-she-drools state and me coming off a week-long (doctor’s prescribed) pill binge, so accompanied by a slew of engagement rings, we were quite the unapproachable force of women to be reckoned with—or so we thought.

Discounting the eighty-seven year old blind man who proclaimed us to be the best looking group of ladies in the Hamptons that summer as he stumbled out of the Saltwater Grill, we thought we were free and clear of being hit on for the remainder of the weekend. But luckily, for material’s sake, that was far from the case. Apparently, half-conscious girls and diamond rings don’t scare off boys in the Hamptons.

Next came Phil, a twenty-four year old who bought us a round of drinks with his father’s Amex at Dunk Deck, and proceeded to talk our ears off for approximately thirty minutes about how Boy Meets World was the most underrated show of the 1990’s as his father nodded approvingly from across the pool. Emily then proceeded to give Phil a fake number after emptying her glass and we all could only hope we wouldn’t run into him back in the neighborhood—after all, there’s only so much one can discuss if Fred Savage is involved.

After a sloppy Sunday at Boardy Barn, a cab driver named Tiger, and a beer shot-gunning party that rivaled that of a college football team, post-game victory, it was off to The Drift to see the Tin Lizzie vets in action, wearing red, white and blue Spandex from head to toe. It was a sea of Vineyard Vines and Ithaca stripes, with talk of what year they gradated from Cornell and where their shore house was on Dune Road. There wasn't one non-button-up shirt in the house, creating an alarming landscape of pastels and collars.

I had never planned on meeting my uptown prince out East, considering the Hamptons are essentially the drinkers of the Upper East Side transplanted for the summer weekends that fall between Memorial Day and Labor Day, but I knew I was in singles hell when a twenty-something in a pink button-down and khaki pants asked me if I vacationed in Nantucket.

“Do I look like I vacation in Nantucket?” I asked politely as possible, as I motioned to my friends who had just shot-gunned their seventeenth beers of the day in the middle of the bar, which was (proudly) followed up with a College of Wooster-style “boneyard” finish.

I didn’t own an ounce of Khaki, despised Vera Bradley and was disgusted by Lily Pulitzer. I appreciate men who wear t-shirts that fit them properly, rather than Schmediums, and I don’t give a sh*t if you know how to sail a boat or were on your Ivy League school’s rowing team. I want nothing to do with Massachusetts’ vacation towns or the men that frequent them. Again, is that so much to ask in a bar filled with single, good-looking men?

I finally threw in my towel, and my liver, after a nineteen year old asked me if I had kids because I was twenty-eight and lived on the Upper East Side. Have your balls even dropped? I thought to myself as I shook my head at his confused face framed with floppy, verge-of-Bieber hair.

So on that note, happy Hamptons, Upper East Side! Let the summer games begin and congrats to those (a.k.a. my BKM ladies) who never have to worry about playing those games again! And until then for this Sex & the Upper East Side gal, my search for summer love continues…