Here is a real question, which I am not ashamed to admit has been bothering me. I’ve now spent almost five years living in New York, and I’ve met and sometimes charmed all kinds of people, many of them quite well connected and well off, but none has ever asked me to spend the weekend at their (or their parents’ or their ex-husband’s) place in the Hamptons: Why? They call it going “out East,” and every year, when summer rolls around, someone more privileged than myself asks, “Are you out East?” And I fill up with some shame, knowing I could probably be a much better social climber if I really put my heart into it.
And so, for the inaugural return of this column, I decided I would, finally, make my way out East, if not to someone’s hedge-funded mansion, then to a nightclubby retreat, the Surf Lodge in Montauk, which, if you aren’t familiar with it, is located at the farthest end of Long Island (3.5 hours by train, but I took the bus). Montauk is not, technically, in the Hamptons. It’s certainly not the genteel, privet-hedged, socialite-and-moguls Southampton or East Hampton, but rather the nearby hamlet where their younger, thirstier selves go to party, and a good base-camp for my forays into various actual-Hamptons. The Surf Lodge itself is an upscale roadside motel run by a smokeshow Brazilian American businesswoman named Jayma Cardoso, who turned it into a concert venue back in 2008. Everyone from Lauryn Hill and John Legend to Willie Nelson and Jimmy Buffett have jammed out at the Lodge. Courtney Love, I’ve been told, stayed there once and later almost didn’t leave, asking the staff to go fetch her cigarettes from the nearest gas station in the mornings, which sounded like something I might do myself. The place is kind of like the upmarket fisherman’s-village take on a bottle-service clubsteraunt in Manhattan. It’s not easy or cheap to get into, so I was lucky that it was one of the “quietest weekends of the year,” as I was told several times, which is probably why they were kind enough to gift me a place to stay so I could finally pop my Hamptons cherry.
Was it the high-rolling, real-estate-porn perusing weekend I’d always imagined for my first trip to the Hamptons? Not necessarily, but I did have a good time getting messed up in Montauk with the townies and the tourists. As a Surf Lodge employee advised me when I arrived, “If you’re behaving, you don’t belong in Montauk.”
Friday, 2:04 p.m., The Jitney | On Sex and the City, the girls take a bus to the Hamptons. So of course I also opt for “the Jitney,” which Carrie described as “just like the bus to summer camp.” These days, it seems more like the equivalent of flying Spirit Airlines. (I only found out later that there is now a more business-class-esque Blade-sponsored coach that serves espresso martinis onboard.) I take a seat next to a teenager who spends the next four and a half hours banging his head on the seat in front of him while listening to heavy metal, which I can hear clearly through his headphones. In front of me, a woman wearing Crocs leans her seat back against my knees and falls asleep. The clean-cut corporate gay across the aisle watching Bridgerton also knocks out and starts snoring. A bus attendant hands out free Goldfish, and I discreetly crack open a hard seltzer to wash them down.
Friday, 7:00 p.m., Surf Lodge | Finally, I reach Montauk. On deck at the Surf Lodge, where a crowd of somehow already well-tanned straights is fist-pumping to a house DJ, I meet up with Alan Rish, my Hamptons sherpa who invited me here this weekend. He tells me about his extraordinarily impressive party-boy life: He was a busboy at Studio 54, counted Andy Warhol as a guest at his 25th birthday, and was once very friendly with Bret Easton Ellis. For the past 16 summers, he’s been coming to the Surf Lodge. “Montauk” — Andy himself once owned a compound down the street, and the Rolling Stones used to come hang out nearby — “Used to be more artistic,” Alan explains to me. “Now it’s more party.” It appears so …
Friday, 7:42 p.m., Surf Lodge | It’s sunset — a very important time of day, I was told by several Hamptonites over the weekend, who seem to think their sunsets are uniquely beautiful — and everyone is smiling, drinking, dancing. I quickly recognize a blondie I know, who on Instagram seems to spend most of her time here drinking Aperol Spritzes. “You can’t come to the Surf Lodge without seeing Ruby! It’s a rite of passage!” she screams at me, before turning her attention to her best friend “Kitty.” That would be the shockingly pretty Kit Keenan, a TikToker, onetime Bachelorette contestant, and the fashion designer Cynthia Rowley’s daughter. When I ask them what I should do to have a good time, they recommend that I go play “padel”: apparently, that’s a fancy word for racquetball, which they call “the Hamptons summer sport.” To be frank, that’s not exactly the kind of fun I was talking about. Then again, they say all the “well connected” “hot boys” play.
Friday, 10:50 p.m., Surf Lodge | It’s getting sloppy real quick in a good way (someone later told me this is commonly referred to as “the Slodge”). Every few minutes, the crowd collectively chants, “5, 6 … 5, 6, 7, 8” and then drops to the floor. I go out for a smoke and meet two girls — one in a skimpy red dress, the other in combat boots — puffing on a weed pen. They tell me they’re here with a bachelorette party, describing the bride as a “Gossip Girl kind of girl”; she’s obsessed with the episode where Serena and Dan have sex on the beach in the Hamptons, which is how they ended up here instead of Nashville for the bachelorette trip. Eventually, the Surf Lodge closes, and their friends come out slurring, “EVERYBODY ON THE BUS.”
Friday, 11:15 p.m., Party Bus | And just like that … I’m on another stinky bus, this time with 20 girls from Ohio. “Look at all these goddamn beautiful women. You’re one of us. You’re one of us! We’re a stunning group of women, and you’re a part of it. You’re fucking invited,” one sloshed girl named Tory tells me, while the others twerk and twirl. I didn’t expect to be so gender-affirmed on the party bus.
Friday, 11:49 p.m., Bounce | We head around the corner to Bounce, a beachside nightclub that was once called, incredibly appropriately, the Sloppy Tuna, where, as one person put it to me, “frat boys go to barf.” Inside, we spot a white girl slapping a literal little person’s ass on the dance floor. There is a gratuitous amount of fist-pumping here, too.
Saturday, 1:34 a.m., Bounce | My new girlfriends depart on their party bus, and I glom onto a group of finance girls with perfectly frozen foreheads visiting from Manhattan. They’re disappointed in the buffet of men with fades on display. Also, unfortunately, they all seem to be “about five-eight.” They are especially appalled by a bro in the corner who is trying to lift his friend up onto his back. “Like … what?”
Saturday, 1:35 a.m., Bounce | Me and the consultant babes are rolling our eyes at these men when a beefcake in a Bass Pro Shop cap with a sunburnt neck stumbles over double fisting a beer and a frozen tequila sunrise, which he’s drinking because he asked the bartenders for the “gayest drink they could make” (Happy Pride!). He tells us he’s a member of the Coast Guard stationed in Montauk and attempts, unsuccessfully, to flirt with the girls. He’s a creep. “I’m like a first responder, you know. I rescue girls from alcohol,” he says. They roast him viciously, pointing out that he has comically small hands. “I’ve never seen smaller hands in my life,” one of them giggles. “You know what that means!” squeals another. “I’m pretty insecure,” he responds sheepishly. I order an Uber back to the Lodge.
Saturday, 5:14 p.m., Grey Gardens | The next day, after some much needed rehydration, I decide I should probably do something slightly more … elevated. A little more East Hampton. Luckily, I’ve been invited out to a cocktail party at Grey Gardens — the pedigreed house that was originally featured in the famous Maysles Brothers documentary (you can also read Gail Sheehey on it from 1972). The event was hosted by a local social-climbing rag called Hamptons Social and the fashion brand Figue. After Big Edie died, Little Edie sold the house to the Washington Post big shots Ben Bradlee and Sally Quinn. In 2016, it turned over (for $15.5 million) to the Figue designer Liz Lange. She gave it, in her words, a “major, major, major gut job.” The result, even though we were only invited into the gardens, is spectacular. There is a big glittering pool, a grass tennis court, and plenty of immaculately trimmed landscaping. (Still, Lange says it can be an occasionally annoying place to live: “I’ve found strangers wandering in our gardens”; I notice a security camera in the treetop.) Almost everyone who arrives — mostly women in floral sundresses and Candace Bushnell — immediately grabs a cocktail and then scurries off somewhere on the property to take selfies. This will later become lots of gloat-acious social-media material. A guy with an acoustic guitar starts playing “Three Little Birds.” But of course every little thing is going to be all right here.
Saturday, 6:00 p.m., Grey Gardens | Two people recommend I go to the restaurant Duryea’s while I’m in town for its “famous” Lobster Cobb. It costs $97. I think I’ll opt for the free catering — oysters, beef tartare, fried zucchini flowers — which as the editor of Hamptons Social makes sure to inform me, is a favorite of Kelly Ripa’s.
Saturday, 6:15 p.m., Grey Gardens | I have the pleasure to be introduced to the former mayor of Southampton, Jesse Warren, who’s kind of like a handsomer, straighter Pete Buttigieg. He’s no longer in office, but he starts stumping. He tells me he got involved in politics after Trump was elected — “I felt like I needed to do something” — which reminds me of the fact that I saw three MAGA flags on the way to this very party. Apparently, being mayor of such a tony place isn’t all garden parties and free-flowing rosé. “Southampton is extremely political. And there’s a lot of special interests. A lot of money,” he says. His wife, an icy dye job in an LBD, tells me she just heard about “a documentary that apparently everyone has seen.” I find a hair in my rosé. Isn’t that ironic?
Saturday, 6:50 p.m., Grey Gardens | Time to skedaddle before I trip into the pool or do a Little Edie flag dance. Outside on the street, Neil Patrick Harris’s husband is trying to direct traffic, since a bald guy seems to have fallen asleep on the street in his Audi.
Saturday, 7:16 p.m., Pierre’s | Earlier in the day, when I’d been desperate to find something … special to do tonight, I DM’d and emailed just about anyone I could find on social media who was posting about being “out East.” I contacted Summer House cast members and Instagram influencers and one guy I know who got rich selling fancy shower heads. The only person to respond to my desperation is Kelly Killoren Bensimon, the former New York “It” girl turned Real Housewife turned Realtor. She invites me out for a drink at a French bistro in Bridgehampton. There I find her in a pink miniskirt with her daughter, some friends, and their fluffy lap dogs, Tarzan and Lottie Loo. I’ve been fortunate enough to get tipsy with a number of Real Housewives, but she’s probably the sweetest, the most down to earth I’ve met. “Welcome to the Hamptons. I’ll be your cruise director,” she says. She serves me some more rosé with ice chips — which, she informs me, is what the French call “piscine.”
Saturday, 8:00 p.m., Pierre’s | As we continue to rosé all day– “Swan vibes! Hanging out with Kelly Bensimon! Rosé!” Kelly squeals — she tries to convince me, unnecessarily, about the special perks of life here. This is a “safe place,” she says, where you can “really be yourself.” There’s so much “harmonious love.” She first came out here as a teenager when she was working as a model; she even wrote a book about it for Assouline once. Tomorrow, she’s planning on going out to the polo club to learn how to play. “It’s such a beautiful sport. Outside of rosé, everyone needs a hobby,” she says. “The trainers here are beautiful,” her friend tells me. “You just want to enjoy life,” Kelly continues. The stars start to come out, and out here, you can see them.
Saturday, 12:19 a.m., The Stephen Talkhouse | Pretending like I’m a bougie housewife is nice and everything, but eventually I decide it’s time to come back down to earth myself. Somehow, I get to DM’ing with a nice gay who’s also visiting from the city, and he tells me he’s going to be hitting the local bars with his friends, who are all “queer, mainly female identifying farmers.” I guess there are a lot of farms out here — I suddenly remember a roadside sign I saw for “local asparagus” — and on their property, they tell me, “the only boys are billy goats.” They sound like my kind of people. I meet them at Stephen Talkhouse, a live music club in Amagansett which was described to me as a “townie bar.” Tonight, a boy band called Faces for Radio is playing covers of “Wonderwall” and “Stacey’s Mom,” and the townies are fucking loving it. After “toiling toiling toiling toiling” in the fields all day, these farmers are ready to boogie. “I wanna be in there rocking out with my cock out with bullshit people. I want to dance my little coochie off,” the gay tells me. We all get wasted on Miller Lites and lose ourselves on the dance floor. “You’re seeing the real Hamptons, rather than the bullshit rich people. Fuck that.” On the way out the door, a girl named Lexie Loo bums me a Parliament: “It’s an empathetic cigarette. That’s what I always say. It gives back.”
Sunday, 5:13 p.m., Surf Lodge | Everybody — from Grey Gardens to the slopfests at Bounce and Talkhouse — has been stressing to me that the best time of the week is Sunday at sunset — there’s that sunset again — at the Surf Lodge, when there’s a weekly concert. Last weekend was 50 Cent, but this week it’s a 28-year-old white rapper named … Yung Gravy, whose 2017 breakout hit was *checks notes* “1 Thot, 2 Thot, Red Thot, Blue Thot” (the lyrics: “Gravy on probation, now I’m off probation / Ayyyy, and I’m fucking with some Asians, ay”). Rumor has it he once dated Addison Rae’s mom. He’s single now, though, which is “good for business, good for being a sex-symbol type,” he tries to convince me, when I get invited to join his crew for tequila espresso martinis (“espresso martinezes”) and sushi before the set. He spends most of the time ogling at the Kendall Jenner types at the next table — “They’re all baddies,” he says. They’re all working models from the city, so “Gravy,” as everyone calls him, asks them to participate in an impromptu photo shoot for his merch. They willingly oblige.
Sunday, 7:30 p.m., Surf Lodge | After several days of dancing to music I’m not quite acclimated to — I guess like everywhere right now, there’s been a lot of country this weekend, and not just Beyoncé, which might or might not be a sign of the way the election is going — and despite my better impulses, I decide to sit back and stick around to watch Yung Gravy send the crowd into the last dance of the weekend. Even though I see one girl in Balenciaga sunglasses with her nipples out, some people even show up with their toddlers, and a boatful of local boys pulls up on the pond next to the stage and strips down to their Speedos. Another rosé drinker in a KORN hat yelps that she’s “feeling really good.” “Is anyone trying to get romantic with Yung Gravy tonight,” Gravy calls out to the crowd. Several women excitedly raise their hands. I do not, but I can’t help but giggle when he launches into his new song of the summer, which is not a totally inaccurate way to describe my weekend: “Drugs, Money, Pussy, and Beer.”
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