The Flack Files: How to Date in the Hamptons

by The Daily Front Row

Illustration by Julie Houts

Our fearless flack is a seasoned observer of East End dating. As the summer scene heats up, she lays down the law on how things should—and should not—be done. Sorry, boys—as of the moment, she’s taken!

Dearest Hamptonites,

As we prepare for yet another raucous, party-filled weekend out East, a quick primer on navigating summer romance:


Make sure to save a guy’s number in your phone as “Ryan Ruschmeyers” or “Tim Talkhouse.” “Harry Hamptons” is far too vague the next morning. I’ll never forget the time I sent a racy pic to “Steve Hamptons.” Too bad Steve was my cab driver…

Avoid the guys you meet at “influencer” house parties. Some brand of personal care products likely bused him in on a Greyhound, and he definitely doesn’t have a place to stay—unless at your place, perhaps?—or a 401(k).

Remember the Hamptons are really big, yet really small. You could end up at a super awkward brunch at Sant Ambroeus when Mr. Smitten Southampton bestows the honor of introducing you to his childhood bestie, whom you casually tongued in Montauk over MDW. Check, please!


Fret if you don’t meet a guy out at the bars. You’ll have an even higher chance of a love match if you share a cab home with strangers.

Be the “homeless” Hamptonite. We’ve all been there—your house is in Bridge, the party is in Montauk, and the creepy cab driver is demanding you pay him $200 for a 2 a.m. ride home. It might seem like the most economical option to just shack up with a virtual stranger, but you certainly don’t want to be divvying up bagels with Mr. Right Now and the contents of his share house the next morning.

Attempt intimacy on a sheetless air mattress after skinny-dipping with your crush. The excruciatingly disturbing sound of flesh on wet rubber is something that will haunt you for the rest of your life. Or so I’ve been told. Side note: Always make sure to collect those undergarments that were wantonly flung into the lawn pre-plunge. There’s nothing more mortifying than stumbling upon a pair of neon pink Hanky Pankys in the lawn the next morning. Note to self: I’m officially too old for neon pink underwear.

Attempt to bring your first date to the Surf Lodge if you expect to receive any form of undivided attention. I’ll never forget when I met a hopeful Hinge match for one of the Lodge’s famed summer concerts. I made the distinct mistake of wearing a lovely Sea sundress (full coverage, just enough cleavage), whilst the nubile ladies of Montauk were hawking all their feminine wares. Crop tops, underboob, fringe butt huggers…the horror! Then again, this is an excellent test of the roving eye.

Worry about getting serious until late August. Let relationships evolve naturally, and enjoy this time to create special Hamptons memories. One of my favorite moves is to find a way to casually take the train home. Couples that train together, stay together. That said, there’s nothing more divisive than seeing how one handles the departure at Penn Station. If you’re riding up the escalator hand-in-hand to go get Sunday Scaries Seamless, I like your odds. The quick pat on the shoulder, followed by a dash to the cab line? You’ll probably be fodder for next season’s dating column.


Your Favorite Party Pooper

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