Bill Gates’s Biggest Regret: Letting an Old Love Slip Away

When Bill Gates called his divorce from Melinda French Gates the biggest regret of his life, he explained that when they met, in 1987, he wasn’t yet the mega success that he is today.

“There is a certain wonderfulness to spending your entire adult life with one person because of the memories and depth of things you have done and having kids together,” Mr. Gates, the billionaire co-founder of Microsoft, told The Times of London in a recent interview.

“When Melinda and I met, I was fairly successful but not ridiculously successful — that came during the time that we were together,” he continued. “So, she saw me through a lot.”

Mr. Gates’s wistfulness about an ex who was by his side for decades highlights the premium that the rich and famous have long placed on relationships that began before the arrival of wealth and fame. For many successful people, these relationships — whether romantic or platonic — are sacred precisely because of their roots in shared experiences, hardships, wins and love that predate their changing fortunes. A time-tested bond, after all, is one of the few luxuries money can’t buy.

It’s a classic pitfall of the nouveau riche (or nouveau célèbre) to ditch the Day 1 partner — the one who stood by you for better or for worse and when you had very little to your name — for someone who is younger or more attractive. While that wasn’t exactly the case for Mr. Gates, who had already amassed a great deal of money when he met Ms. French Gates, he certainly wasn’t as powerful then as he was when they officially parted ways, in 2021.

Importantly, he also didn’t initiate his own divorce: Ms. French Gates was reportedly unhappy with the way her husband had handled previously undisclosed sexual harassment claims against his money manager and she was uncomfortable with his relationship with the disgraced financier and convicted sex offender Jeffrey Epstein. (Representatives for Mr. Gates did not immediately respond to requests for comment on Thursday.)

People love a romantic rags-to-riches story about lovers who see each other through their humble beginnings. When Michelle Robinson met a young law student named Barack Obama in 1989, the future president was living frugally and driving a beat-up car that had a four-inch hole in the floorboard. Despite her suspicion that he might never make any money, the future Mrs. Obama stuck by his side.

“Life with Barack would never be dull,” she wrote in her 2018 memoir, “Becoming.”

But is sticking around always worth the risk? When it comes to romantic relationships, many young women online are being cautioned to not stay with a partner who doesn’t have much going for him.

According to Sabrina Zohar, a dating coach on TikTok, it’s best to avoid such a situation because “you’re putting a bet on a hypothetical.”

If the person “standing in front of you is not the match for you,” she says in a 2023 video, “then stop engaging and continuing to put yourself in this ‘prove it’ mentality.” (If Michelle Robinson had listened to similar advice, it’s possible that there never would have been a first lady Michelle Obama — or, for that matter, a President Barack Obama.)

It’s not just longtime romantic bonds that people are protective of but their friendships too, especially after they have achieved a high level of success. In their 2018 song “Friends,” Beyoncé and Jay-Z rap in praise of longtime friends who have had their backs over the years, looking down on peers with newer, less trustworthy friends. “I don’t know what I would do without all of my crew, yeah / I ain’t makin’ no room, yeah, I ain’t makin’ no new friends,” Beyoncé asserts. (Five years earlier, Drake expressed a similar sentiment in DJ Khaled’s “No New Friends.”)

The year that Bill Gates met Melinda French, she was a new hire at Microsoft and he was on the cusp of becoming the world’s youngest billionaire ever at the time. She was with him when Microsoft debuted Internet Explorer, when Queen Elizabeth II made Mr. Gates a knight and when Time magazine jointly named the couple (plus Bono!) a “Person of the Year” for their philanthropy work. By the time they ended their 27-year marriage, they had put three of their own kids through college and mosquito nets over the beds of hundreds of thousands more.

For Mr. Gates, the sadness of his ex-wife’s departure from his life might have been slightly tempered by her continuing role in the Bill & Melinda Gates Foundation, which the couple started together in 2000. When she announced last spring that she would be resigning as a co-chair of the organization, she was functionally severing one of their oldest and most prominent ties as a couple.

“I was disappointed that she took the option to go off,” Mr. Gates told The Times of London.