Being Born in the Hamptons Is One Thing. Staying Is Quite Another.

Robyn Diederiks-Henderson grew up in Montauk, N.Y., waiting tables at her mom’s restaurants. Her longtime boyfriend and husband of two years, Dylan Henderson, was born and raised down the road in Southampton.

But birthrights get you only so far in Long Island’s most famous resort towns.

“Because we weren’t born into money,” Mr. Henderson said, “it feels like breaking into the billionaire’s club. It can be disheartening to live in Southampton, to have been born and raised here and feel like there’s not a space for you anymore.”

After they met and decided to live together, the couple shared their first home with roommates. In their mid-20s they couldn’t find any place to live and had to move in with Mr. Henderson’s mother.

They saved and eventually found a two-bedroom apartment they could afford on 27East.com, a news and classifieds website for the Hamptons. They’ve kept the place for four years now — and even managed to negotiate a rent reduction during the pandemic. But they moved in when it was just them and their oldest son — Remington, 12 — and two years ago their second son, Charlie, came along.

“The walls are slowly shrinking,” Ms. Diederiks-Henderson said, laughing. “Because we’re growing.”

While they’re grateful to have housing at all, their current living conditions aren’t sustainable. “It’s not an ideal situation,” she said. “We’re on a main road and our kids can’t play outside, we don’t have laundry and the baby sleeps in our room. Normally you would move on, into a bigger home to accommodate your family, but we’re not able to do that because of the rent in our area.”

The couple are willing to look for places farther away, places that could make their commutes an hour or longer, but there are meaningful attachments to the immediate community where they’ve lived for the past four years.

“My son’s autistic and the school here is extremely important to us,” Ms. Diederiks-Henderson said. “Keeping him here where he’s gone to school his entire life is important.”

The Southampton Union Free School District “is incredible.,” she added. “They’ve done pretty much anything we’ve ever asked of them.”

Both Mr. Henderson and Ms. Diederiks-Henderson bring an entrepreneurial spirit to their community. She runs Robyn’s Kitchen, a personal chef business, and he runs Finesse Athletics, a personal training business.

“I’ve been training for eight years,” Mr. Henderson said. “During the pandemic, the gyms were shutting down and I had the knowledge.”

He decided to start his business. “It was really, really scary,” he said.

$1,500 | Southampton, N.Y.

Robyn Diederiks-Henderson, 32; Dylan Henderson, 31

Occupation: She is a personal chef, and he is a personal trainer.

On entrepreneurship: Ms. Diederiks-Henderson was waiting on tables at a luncheonette when a customer asked if she would help serve a dinner party. She arrived 30 minutes before the dinner, and the client was overwhelmed. “I ended up cooking a dinner party for the first time in my life,” she said. “Someone at that party called me the next day to ask if I could cook for their family for the summer. They offered me more money than I ever thought was possible to make cooking. And that’s when it occurred to me, ‘Oh, I can actually make a living out of this.’”

On sobriety: Ms. Diederiks-Henderson and Mr. Henderson got sober together a few years into their relationship. “We figured out how to be real people together,” Ms. Diederiks-Henderson said. “We were pretty major alcoholics and drug addicts, and we didn’t know who we were yet. I found myself in cooking, and he found himself in fitness. Now I know that fear is not a word in my vocabulary. Life’s all lessons. That’s something I’ve learned through sobriety.”

Mr. Henderson and his wife maintain a steady roster of clients. But their workflow mirrors the seasonal flow of summer visitors to Southampton.

“If I was able to make summertime money year-round I would — perhaps — be able to afford a home here,” Mr. Henderson said. “But because it’s such an ebb and flow, it makes it really difficult. We live with a lot of financial insecurity.”

There is a fundamental conundrum that comes with keeping roots in a major tourist destination: The influx of visitors that provides income is the same influx that makes the cost of housing so out of reach.

“There’s a tension in the summer between visitors and people who live here,” Ms. Diederiks-Henderson said. “We just don’t have the resources for that amount of people. It still blows my mind that people are still allowed to build on new land out here.”

She remembers growing up, when she and her friends would make fun of people from Manhattan. “We would say ‘citi-diots.’ That was just an ignorant term we’d use as teenagers. The crazy thing is when I look back at how things were then in terms of visitors, it was nothing compared to what it is now. At the same time, I’m an adult now and I see people as people, not as objects. So the tension that exists out here isn’t necessarily with the people but with the lack of resources. There’s a little bit of bitterness.”

It can be isolating, carrying this bitterness while immersed in the seasonal wealth of the town. “All of my clients are well off,” Mr. Henderson said. “Everyone I come into contact with, business-wise, has enough money to hire a personal trainer, so they don’t have the fear and insecurity when it comes to housing. They’re the ones who are coming here and buying the homes. That’s why I have a difficult time with these dynamics.”

He and his wife both remember homes from their childhood neighborhoods that sold for around $100,000 and now routinely hit the market for millions. Ms. Diederiks-Henderson marveled at a trailer in Montauk that recently sold for $3.75 million.

“My best friend grew up in that trailer park, and I remember making fun of the kids who lived there — being the high and mighty third grader that I was,” she said, laughing. “But now people can’t afford to live there. That’s the whole point of a trailer park! You’re supposed to be able to afford it.”

When the couple have looked for a bigger apartment or a house to rent, they haven’t been able to find anything workable for less than $12,000 a month. “Pay anything less,” Mr. Henderson said, “and you’re getting a shoe box. That’s for a yearlong lease. If people do summer rentals they can get $100,000 a month, depending on the location. So, it really messes up the whole market. Airbnb destroyed year-round renting. If you can get $1,500 or $3,000 a night, you’re going to do it.”

Ms. Diederiks-Henderson said her husband harbors a fantasy that they’ll meet an older couple who will sell them a house at a favorable price because they want to prioritize selling to a local family. “Why would they do that?” she said. “That’s not the kind of world we live in. Why would they not try to make as much money as possible? We’re not taught to do the right thing. We’re taught to make as much money as possible.”

She says that during the off-season she can’t help but notice how many houses sit empty, unused. “I heard recently that about 30 percent of the houses out here are occupied year-round,” she said. “There’s all of us, struggling to live out here. We’re the people who cook, who clean, who provide services, who look after this place. There’s no place for us, and we’re surrounded by all these empty houses.”

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