Odds on Who Bill Gates Will Date Next

By in Entertainment on
6 Minute Read

Earlier this week, billionaires Bill and Melinda Gates announced plans to divorce after 27 years of marriage. The couple says they plan to continue to work together through the Bill and Melinda Gates Foundation, but their time as a couple is coming to a close. In a statement, they said,

“After a great deal of thought and a lot of work on our relationship, we have made the decision to end our marriage.”

So, Bill is set to enter the dating scene at the ripe old age of 65. The Microsoft founder still seems to be in very good health, and there’s something about being worth billions of dollars that seems to make people like him hot commodities on the dating market.

Just a couple of years ago, Amazon founder Jeff Bezos and his wife, MacKenzie Scott, announced they would be getting a divorce of their own. Scott wound up taking home billions as a result of the divorce, and it’s safe to assume Melinda will be doing the same. Regardless, something tells me Bill and his $130 billion fortune will be just fine.

Entertainment betting sites are giving you the chance to wager on Bill’s next significant other. The site has already posted odds on whom Gates may date next. The candidates get pretty wild the further down the list you go, but let’s have some fun with this.

Ann Winblad (+300)

It’s ok if you’ve never heard of Ann Winblad before. Winblad is a 70-year-old that founded Open Systems Inc., an accounting software company, back in the 1980s with three former co-workers. The company quickly saw its value escalate before it was sold for $15 million after just six years.

After cashing out, Winblad took a new job with Microsoft and IBM. She met Bill Gates at a conference in the mid-80s, and the two would go on to date for nearly four years before calling it quits in 1987.

However, the two remained friends. According to an old Time Magazine profile, she and Bill would actually vacation with each other once every year, even after both were married to other people. Here’s the excerpt from the 1997 piece:

Even now, Gates has an arrangement with his wife that he and Winblad can keep one vacation tradition alive. Every spring, as they have for more than a decade, Gates spends a long weekend with Winblad at her beach cottage on the Outer Banks of North Carolina, where they ride dune buggies, hang-glide and walk on the beach.

“We can play putt-putt while discussing biotechnology,” Gates says. Winblad puts it more grandly. “We share our thoughts about the world and ourselves,” she says. “And we marvel about how, as two young overachievers, we began a great adventure on the fringes of a little-known industry and it landed us at the center of an amazing universe.”

…what?? No wonder Bill and Melinda didn’t work out. Bill was off vacationing with his ex-girlfriend at least once a weekend for years, apparently. There’s no telling whether this tradition has continued beyond 1997, but this is obviously the reason Ann Winblad is a +300 favorite to be Bill’s next suitor.

Winblad reportedly got married in 2015, so I’d advise taking a shot on Winblad at +300 if we soon hear that her own marriage happens to be on the rocks. If we don’t, this is an easy one to avoid given the short odds.

Shari Arison (+2500)

Perhaps it’s easier for billionaires to date fellow billionaires. If that’s the case, perhaps Shari Arison could be a good match for Bill. Arison is reportedly worth just under $4 million as the owner of Arison Investments, a firm that oversees several different companies. She’s the sister of Micky Arison, the billionaire owner of the NBA’s Miami Heat.

Arison has already been married and divorced three times, but she seems to be single at the right time. She’s originally from New York City but currently calls Israel home, so she and the Seattle-based Gates would have to commit to something of a long-distance relationship if they are to hook up. There is certainly a feasible link between a couple of single billionaires, but that distance could prove to be problematic.

Julia Koch (+3300)

Julia Koch inherited her vast $63 billion fortune from her husband, David, who died in 2019. The Koch brothers built a lucrative business empire, but they are primarily known as some of the most generous donors to conservative and libertarian causes in American politics. David was even the vice-presidential nominee on the Libertarian Party’s presidential ticket back in 1980.

So, Julia became a widow a couple of years ago. In the process, she became the richest woman in the world after inheriting 42 percent of Koch Industries. She remains on the Koch Industries board of directors, but she isn’t nearly as visible in public life as Bill Gates.

One would imagine Julia Koch has political beliefs aligned with those of her former husband, which could prove to be a roadblock to a relationship with Gates. The Koch brothers are known for aggressively combating legislation designed to address climate change. Gates, meanwhile, recently wrote a book about the impending climate disaster.

Opposites may attract, but it’s hard to see this one working out.

Jennifer Aniston (+3300)

Gates and Jennifer Aniston both became household names back in the 1990s as two of the most famous people in American pop culture. Way back then, Aniston and Friends co-star Matthew Perry were actually hired to lend their respective voices to an instructional video for Windows 95:

I’m guessing Gates had zero actual involvement in enlisting Aniston to help sell Microsoft’s product, but there’s still a link here. Aniston is single after divorcing Justin Theroux back in 2017, so perhaps she and Gates can bond over memories of various computer operating systems from 30 years ago.

We’ve seen stranger couples come out of the woodwork before, so I don’t think Aniston is a terrible bet to be Gates’ next significant other at the current +3300 odds. It’s a reach, but not quite as random as some of the other names we’ll see on this list.

Longshots to Date Bill Gates

  • Alice Walton (+3300)
  • Feliz Sahenk (+3300)
  • MacKenzie Scott (+3300)
  • Sheryl Sandberg (+3300)
  • Laurene Powell Jobs (+3300)

A random cast of billionaire widows, heiresses, and divorcees. Having money probably isn’t a trait overly useful to Bill Gates, so we can avoid this group.

Odds on Celebrities Dating Bill Gates

  • Teri Hatcher (+3300)
  • Drew Barrymore (+5000)
  • Jane Fonda (+5000)
  • Angelina Jolie (+5000)
  • Natalie Imbruglia (+5000)
  • Kim Kardashian (+5000)

Teri Hatcher is another actress that has been married twice in the past, though she has been single since 2003. I’m not entirely sure why her +3300 odds are more favorable than the second gaggle of actresses, singers, and reality stars listed under her, but I suppose there is still an outside chance Bill looks to find his next girlfriend in Hollywood.

As amazingly jarring as it would be to see Kim Kardashian go from Kanye West to Bill Gates, something tells me that the relationship isn’t in the cards. We live in strange times, but even that one seems like a stretch for this particular life simulation.

Hillary Clinton (+6600)

Hillary Clinton divorcing Bill Clinton and swapping him out for Bill Gates would be a dream scenario for far-right-wing conspiracy theorists all over the internet, but that sure would come out of left field. Hillary stuck with the former president during some pretty thin times, so I doubt the two will give it up now that they’re both in their 70s.

Meghan Markle (+6600)

Family drama aside, there is no reason to believe Meghan Markle is unhappy in her marriage to Prince Harry. The two are about to have their second child, and they seem perfectly happy since they moved to the US last year. Money also isn’t an issue if you’re a member of the Royal Family, even if that arrangement is looking a little dicey these days.

No offense to Bill, who seems like a perfectly nice human, but I doubt a 65-year-old former tech nerd would be at the top of Meghan Markle’s wish list if her relationship with Harry went south, anyway.

Crazy Odds to Date Bill Gates

BetOnline has out done themselves yet again, the online betting site is offering odds on people who you would never think of:

Greta Thunberg (+10000)

Excuse me?

Oprah Winfrey (+10000)

What in the name of Stedman is going on here?

Caitlyn Jenner (+10000)

Caitlyn Jenner is a little busy trying to unseat the current governor of California, thank you very much.

Queen Elizabeth (+10000)

I think we’re done here.

Taylor Smith

Taylor Smith has been a staff writer with GamblingSites.org since early 2017. Taylor is primarily a sports writer, though he will occasionally dabble in other things like politics and entertainment betting. His primary specialties are writing about the NBA, Major League Baseball, NFL and domestic and international soccer. Fringe sports like golf and horse racing aren’t exactly his cup of tea, bu ...

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