What It’s Like Dating a Billionaire: Luxury, Private Jets and a Very Strange Rule Before Sex

What happens when an ordinary woman meets a billionaire? The answer might seem obvious: private jets, luxurious homes, exotic trips, a personal chef and a life free from financial worries. But writer Louise O’Neill discovered firsthand that even the most attractive and wealthy man cannot buy something money simply cannot provide — genuine chemistry between two people.

In the summer of 2024, 39-year-old O’Neill was in Ireland but had set her location on the dating app Hinge to London. That was where she met a man named Nate.

He was considerably older than Louise, tall and very attractive. When a friend decided to look him up online, she discovered that his company was valued at more than $1 billion. Nate had a private jet, a luxurious penthouse overlooking Central Park and several homes around the world.

He primarily lived in New York and turned out to be a big fan of talking about wealth and successful living. In their messages, he told Louise about an exclusive billionaires’ club he had been invited to, discussed Burning Man, intermittent fasting, cold plunges, psilocybin and the latest fashionable ways of extending one’s life.

They messaged for an entire week, and Nate clearly found Louise interesting and funny. Eventually, she was the one who suggested that he come to Ireland for their first date.

Nate took the arrangements extremely seriously. He asked which hotel she would recommend, opted for a five-star property and, once they had settled on a location, booked a suite.

Louise had already decided that there would be no sex on the first date. But it turned out that Nate had a rule of his own. He told her that he never had sex on a first date because, in his words, the female body was too complicated and he needed time to “figure it out” — as though he were dealing with a Rubik’s Cube.

But then came an even stranger request.

Nate admitted that he was extremely afraid of contracting a sexually transmitted infection, so before becoming intimate, Louise would have to undergo testing with his own doctor.

That was the first moment the writer began to wonder whether this man was actually right for her.

The second warning sign was his constant need to display his wealth. Photos of his private jet, his enormous penthouse with panoramic windows and lavish bouquets of flowers that he ordered purely for the scent of jasmine and roses — it seemed Nate could not talk about himself without mentioning money.

Still, the first date went well. Nate was just as attractive as he had appeared in his photos and really was around 6 feet 3 inches tall. They spent several hours talking over dinner and seemed to genuinely like each other.

At one point, the man compared Louise with the women his friends dated.

According to him, many of them chose women in their twenties — yoga instructors or beautiful Ukrainian women who wanted a $20,000 Van Cleef & Arpels piece after the very first date. Louise, Nate pointed out, was different.

“You’re sharp,” he told her.

The compliment made her think. She imagined herself among Nate’s friends — men in their fifties and sixties accompanied by much younger, glamorous women. Perhaps she would become a kind of “trophy,” just a different type: a woman chosen not for her youth and beauty, but for her intelligence, career and independence.

Another detail surprised her: Nate barely ate anything. He even complimented Louise for allowing herself a piece of bread, remarking that women in New York had long since given up foods like that.

After dinner, Nate kissed her. The kiss was good, but Louise felt nothing.

Later, they went to the coast and continued talking. Nate had already begun describing what their life together might look like.

If the relationship worked out, they could travel extensively. He usually spent winters in Hawaii, where he owned a house right on the water. Louise could swim every morning. He was also looking at property in the western part of County Cork and could buy another home on the U.S. West Coast if she preferred that climate.

Then Nate began listing the other advantages of his lifestyle. Needed tickets to a Taylor Swift concert? He could get them. A fan of Lady Gaga? She had already performed at his company’s corporate event, and perhaps he could arrange another appearance.

And that was when Louise realized with startling clarity just how easy her life could become if she entered Nate’s world.

She could wake up in her dream home on a cliff in Ireland or in a luxurious penthouse in New York. She would have a personal chef, a housekeeper, a dog walker and a personal assistant. Pilates, expensive beauty treatments, a private jet, luxury hotels and designer clothes.

For a writer accustomed to living with financial uncertainty, it seemed almost like a perfect deal. She would no longer have to worry about whether her next book would earn enough money, whether she would secure another contract or whether she would spend the rest of her life worrying about financial stability.

Nate could give her peace of mind.

But along with that came the most important question: at what cost?

Louise understood that Nate did not seem like someone who wanted to own or control her. He appeared kind and decent. Yet it would still be his life that she would be entering, rather than a life they were building together as equals.

What if she did not want to spend the winter in Hawaii? What if she did not want to have dinner with his friends and their young girlfriends? What if she could not hide her disgust toward relationships that seemed too transactional to her?

And most importantly — what would happen several years down the line?

Nate said he had chosen her for her intelligence. But would he still be interested when she grew older, while his friends’ girlfriends remained young?

Sitting beside him on the stone wall, Louise felt the same emptiness she had felt after the kiss.

After Nate returned to the United States, they continued messaging for several more weeks. But Louise already knew that she did not want to continue the relationship. Eventually, she began replying less and less often, until Nate finally asked what was going on.

He was genuinely surprised and somewhat hurt when she told him that she did not think it was right for them to continue dating romantically.

Louise admits that, from the outside, she may have appeared inconsistent. She was the one who had suggested that Nate fly to Ireland, assured him that the age difference did not bother her, and then suddenly pulled away.

Later, she reread their messages and realized that the man genuinely might not have understood why she had made her decision.

Several weeks later, Louise wished Nate a happy birthday. She wanted to thank him for his kindness and for helping her realize something important through their experience: a person can possess absolutely every quality on her list of an “ideal man” — looks, intelligence, money, generosity and success — and still fail to inspire genuine feelings.

Chemistry cannot be manufactured. And it certainly cannot be bought.

Louise never told Nate everything she wanted to say. She simply wrote that he was a good person and deserved to meet a woman who would love and appreciate him.

They have not spoken since. Occasionally, Nate appears in her social media recommendations, and Louise wonders what is happening in his life and whether he has met another woman.

She does not know what kind of woman she turned out to be — young and beautiful, intelligent, or simply someone willing to share his luxurious world.

But Louise is now certain of one thing: a life in which she had to trade the dream of genuine love for financial security would not make her happy.

Even if the man beside her were kind. Even if he were handsome. Even if he had a private jet, homes around the world and stood 6 feet 3 inches tall.

Louise O’Neill described her relationship with Nate in her new book, A Bigger Life.