From Fantasy to Reality: Experiencing the Hamptons for the First Time

The Hamptons have always been a dream, that far-off place you hear about but never quite touch — like a child imagining the wonder of Disney World, just beyond reach. My fascination began years ago, curled up in my college dorm, lost in the world of Revenge. Emily Thorne, with her carefully laid plans, and Victoria Grayson, who radiated icy elegance, became my personal tour guides to the Hamptons' world of wealth and secrets. Funny thing is, now I often see Victoria Grayson — or rather, her real-life counterpart — in a coffee shop in Santa Monica every Friday. She still has that soul-piercing gaze, the kind that makes you feel like she could unravel your life with just a glance. It’s almost like the Hamptons followed me across the country.

And then there was Gossip Girl. High school, college—those years were shaped by my obsession with the Upper East Side, trying to decipher the allure of New York City and the Hamptons. Chuck Bass was my favorite character on the show, a man whose dark charm and complexity I found myself channeling more often than I’d like to admit. His father, Bartholomew “Bart” Bass, was a billionaire at the helm of Bass Industries, a titan who cast a long shadow over Chuck's life. Yet, it was Bart’s wife, the captivating Lily van der Woodsen, who truly embodied the elegance of that world. She possessed a grace, beauty, and class like no other, effortlessly commanding any room she entered, a perfect complement to the world of power and privilege that surrounded her. Revenge and Gossip Girl were windows into another world—a world of privilege, power, and intrigue. Both shows spun tales of wealth, luxury, and drama, setting the stage for my fascination. To finally experience the Hamptons in real life... it felt like stepping into another dimension entirely, as if I had crossed the threshold from dream to reality, with all its whispers of secrets and opulence.

And then there was Mad Men. That show was my anchor. Set in the very world I would soon navigate myself—advertising executives, tailored suits, and sharp conversations on Madison Avenue—it was more than a show. It was a glimpse of what my life could be, the path I now find myself on. Don Draper was the character I admired most, a figure who embodied the complexities of ambition, reinvention, and the relentless pursuit of perfection. He was the man who could sell an idea with a single, confident glance, a visionary behind the polished façade of 1960s Madison Avenue. Beneath the sharp suits and carefully crafted image, there was a storm—one that made him unpredictable, enigmatic, and utterly compelling. His charm, his flaws, his ability to create something from nothing—it was all part of the mystique that made him more than just a character, but a force of nature I couldn't help but be drawn to. So when the opportunity to visit the Hamptons arose, I knew I couldn’t pass it up. The suits, the sophistication, the marketing genius I once admired now felt like echoes of my own career.

My entry into this exclusive world came via the Supper Club, a private members’ club. In under a year, I’d dined at top-tier restaurants, explored Kyoto and Tokyo, and now this—crossing another dream off the list with a trip to the Hamptons. Supper Club had introduced me to an eclectic, fascinating crowd—plastic surgeons, financiers, writers, Ivy Leaguers—all bonded by a love for impeccably curated dinners. And when it came to planning the Hamptons trip, they left no stone unturned.

Finally, I was about to experience it firsthand. The Hamptons.