For decades, Bill Gates has had an annual ‘long weekend’ vacation with his ex


I saw people talking about some of this stuff in the comments, but I honestly and truly did not know ANY gossip about Bill Gates and Melinda Gates’ marriage. Every profile I’ve ever read about them, they sounded like they complemented each other completely – she was more of an empath, and he was the numbers-oriented brain. But it does seem like there was more drama there than I initially believed. Melinda has already filed for divorce citing the marriage as “irretrievably broken.” But here’s something I didn’t know before this week: Bill takes an annual vacation with his ex-girlfriend??

Before Bill met Melinda after she joined Microsoft as a product manager in 1987, Bill had been dating Ann Winblad, a software entrepreneur and venture capitalist, according to Time. He developed such a strong bond with Winblad that Bill made sure to keep her in his life after they split in 1987.

“Even now, Gates has an arrangement with his wife that he and Winblad can keep one vacation tradition alive,” Walter Isaacson reported in his 1997 Time story on Bill’s life and career. “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,” he told the magazine in 1997. Winblad added to Time: “We share our thoughts about the world and ourselves. 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.”

When it came time for Bill to propose to Melinda, he asked his ex, Winblad, for her permission.

“When I was off on my own thinking about marrying Melinda, I called Ann and asked for her approval,” he recalled to Time in the 1997 story. Winblad ultimately had no qualms about him popping the question.

“I said she’d be a good match for him because she had intellectual stamina,” she told the outlet.

[From People]

Whew, lord. All that money and this is what gets people off – one long weekend once a year with his ex-girlfriend. They ride dune buggies and walk on the beach and talk about biotechnology. I just… well… who knows. Apparently, Melinda was fine with it for a long time. Maybe she stopped being fine with it. Or maybe it was something else entirely. Or someone else.


Photos courtesy of Avalon Red.

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89 Responses to “For decades, Bill Gates has had an annual ‘long weekend’ vacation with his ex”

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  1. Laalaa says:

    Can’t people just divorce without an additional reason?
    I believe they were “just” friends, good friends are hard to find and if people are decent, a married man can spend a long weekend with a long-time friend just as friends. Melinda was cool about it, and they are cool with the divorce. After 27 years, and how many more as a couple, it could just be they want to be honest about their marriage and say – listen, this is not it anymore, and that’s that

    • Ariadne2 says:

      Can’t people just divorce without an additional reason?
      Thank you 👏🏽👏🏽👏🏽👏🏽👏🏽
      Why is it anybody’s business even if something happened the gossip about people’s divorce is always off putting and very disgusting!

    • MissMarirose says:

      Thank you!!!
      Not every divorce has to be some big scandal. Sometimes people grow apart after decades together.
      Ask yourself if you are the same person you were a quarter of a century ago.

    • Seraphina says:

      I agree with your comment. I don’t get this is some passionate love affair. Passion once a year kinda is a long time to wait. But who knows at this point.

    • missskitttin says:

      Maybe they were “open”

    • Lemons says:

      Look, if they want to be billionaires, fine! But when you’re hoarding that much wealth, the public is entitled to some DRAMMMA when you divorce! 😂

      • Laalaa says:

        Hahahaha 🙂 I get that.
        Can you imagine, the things they’ve been through? From regular people to being the richest? But, to be fair, he called it MicroSoft, maybe she wants to experience… an antidote to that? 😉 😉

      • molly says:

        lol. Especially since their kids are now all legally adults. (I don’t like wishing for DRAMZ when there are underaged kids involved.) I want some good ol’ bouncy rebounds out of this!

      • Anna says:

        @Laalaa !!! lol 🙂

    • HeyJude says:

      Honestly, this happens constantly and they’re right in the stage of life for when this happens.
      Their youngest is 18 or 19 I saw in one article. You get married originally, but things change drastically when you have kids and then your life is all kids, kids, kids for however long it takes to get the last one off and on their way in life, you’re distracted by all the chaos of raising them. Then once they’re grown the parents look at each other and are like, “whoa, we’ve really changed as people and don’t have a lot in common as a couple anymore”.

      I can totally see that being the case. Especially if the most scandalous thing we have heard on Bill is an annual adventure weekend trip with a friendly ex.

  2. SusanRagain says:

    The very rich really are different from the rest of us.

    • Gigi LaMoore says:

      Not necessarily. I was on a cruise with two adulterers who told their spouses they were on girls/boys trips, but would instead meet up every year. Poor people just do it on a less grander scale.

      • BlueToile says:

        Interesting. This sounds like that Alan Alda /Ellen Burnstyn movie from the late 70s called “Same Time Next Year.”

      • EnormousCoat says:

        @Bluetoile I was thinking the same thing & now I want to watch that film again.

      • Juniper says:

        @BlueToile and @EnormousCoat, thank goodness I’m not the only one who remembers this movie!

  3. hanna says:

    Or maybe shes not with him on the whole “preassure oxford to patent the vaccines and let people continue to die”-thing? If not, around 40-60 % of the worlds population would have been vaccinated by now. I would be mad.

    • SomeChick says:

      this is my theory. she is a caring and decent person. his choice to knowingly let people die so that big wealthy corporations could profit from the vaccine is vile. she likely wanted no part of that.

      • AnneSurely says:

        This is what I think too. Folks like to portray nerds as lovable, cuddly, misunderstood socially awkward goofs but I’ve known guys like Bill Gates and they tend to be emotionless bots, eating junk food, playing video games, and playing devil’s advocate. I would imagine that grows old very quickly.

      • Anna says:

        Right @AnneSurely I don’t think anyone can amass that much wealth–in the billions–without being a major human rights abuser. Honestly, I just don’t see it.

    • Anna says:


    • A says:

      You all know that’s not the reason right. There are lots of problems with the Gates Foundation outside of this vaccine patent thing, all of which Melinda Gates has been supposedly fine with for years before now. Why would this be the straw that broke the camel’s back? The idea that this incredibly rich white lady called it quits with her husband bc “she cares too much” goes to show just how much grace people will extend white women, to the point of writing straight up fanfiction about it.

    • BrainFog says:

      My (only) theory aswell. This guy has been promoting himself as such a nice one for all these years, but let’s not forget the shady stuff that leveraged part of why microsoft is now as big as it is, and then there was this nice article over at pajiba (i think) recently on how he or his organisation are slowing down the vaccination process over intellectual property… not great, really not great. I was thinking that if she really is as caring as she claims to be then maybe that could have been a factor.

  4. Leonelda says:

    Oh wow it is kind of like a book I read last summer called “28 summers” based on the movie “Same Time Next Year.”

  5. Zapp Brannigan says:

    So who did Mrs Gates get to spend a long weekend with every year? You know since everything was so cool and easy breezy?

    • equality says:

      Maybe she and this woman’s husband got together.

      • Anna says:

        Haha! Did that once after a break-up. We hooked up just to piss off the cheaters. It worked. Still was brokenhearted but at least we both got some hot revenge.

  6. My3cents says:

    I guess you really have to be evolved for something like this.
    I can even imagine a scenario where the two families meet up for a long weekend, but just the two exes is too much.

    • april says:

      Totally agree. I never would allow my husband to do that. Not surprising their marriage is ending with this going on yearly. I would have so much pent-up anger and frustration with my husband for doing this. What message does this yearly event send to your kids?

  7. FHMom says:

    The weekend once a year with the EX was public knowledge from the beginning. It isn’t some kind of smoking gun. Supposedly, they are just friends.

  8. Veronica S. says:

    I mean…I literally lived with my ex and his wife and helped raise their kids for awhile. There was nothing romantic about our relationship, and I am good friends with his wife. So I don’t automatically assume it’s inherently an affair. It’s more his immense privilege that would make me think that since people at that level of money just never have to compromise for anything, so you have to imagine that winds up filtering into issues in personal relationships.

    • Suzz54 says:

      I am very close with my husband’s ex-wife. When my husband and I got serious and time for me to meet his son. I wanted to know it was ok, with her. She was very moved by this and our relationship began…. 13 years later our son is finishing his sophomore year in college. I never worried about my husband or his ex getting back together. They married too young and learned they were friends.., We are a cool modern family. So, I agree Bill and his ex are most likely friends.

    • cassandra says:

      That’s an excellent point about privilege. It’s just like celebrities. I imagine Bill Gates hasn’t heard the word ‘no’ in his professional life in over 30 years.

    • AmB says:

      Good point about privilege, Veronica. But it sounds like there may be something else in play if he “asked her approval” to propose to Melinda.

      • Desert Lizard says:

        Exactly. It’s one thing to stay friends with an ex. It’s another to ask her approval to marry. Ask her opinion maybe but approval? That doesn’t sound right to me.

    • FYI says:

      It’s not comparable. Having the spouse THERE with you is not the same as vacationing alone every year with an ex.

  9. candy says:

    If my fiance had to ask his ex for permission to marry me, I would be outta there. That is not a good way to start a marriage, that and the ongoing “vacation” or hall pass or whatever.

    • Carmen-JamRock says:

      Exactly! “Permission????” If ann were a male friend, would he ask his “permission” to marry? I hope melinda knew of this arrangement before the marriage and knew what she was getting into.

    • Cisne says:

      Hard Pass!!!

  10. Cava24 says:

    The only source for the weekend with the ex story is from 1997. A quick google search shows that she married Kevin Kline’s brother a few years ago. Some kind of ongoing affair seems like a lot to infer based on reporting from the late 1990’s.

  11. Willow says:

    He asked his ex-girlfriend for her approval to marry his current wife??? What the what??? Sounds like emotional cheating to me. I wonder when Melinda found out about this. So sad.

    • Katherine says:

      I don’t know I’m not sure. Maybe it was. It kind of has a weird vibe to be a passionate ongoing romantic affair though. My parents are amicably divorced and split once my siblings and were grown. They are each other’s best friend and will 100% openly state that about each other. They both have other partners and are in happy fulfilled romantic relationships. They (my parents) recently took a short road trip to deal with a financial matter on a mutual property they still own. Separate hotel rooms separate expenses but they had an epic blast. Not really the exact same thing here but I’m just offering an anecdote that adults, especially older adults with some life and relationship experience behind them can navigate friend vs romantic relationships in surprising ways without it always being questionable. I honestly think if either of my parents married their partners they’d ask the other one to weigh in, as their friendship and support of each other means something. Approval is a weird word here that does give me pause but none of us know the exact context I guess. TLDR boomers can be surprising in their later in life adult friendships and relationships.

  12. Melissa says:

    It does make me wonder, if he spent the same weekend every year with a man who got him on an intellectual level and they could hang glide and talk biotechnology with…would we automatically assume sex?

    • Goldie says:

      If the man was an ex-lover of his… then yes.
      But maybe they just stayed friends and Melissa was fine with it. Who knows?

    • whatever says:

      Well, if he had previously been involved in a romantic relationship with that man, then yeah, probably.

    • Melissa says:

      Fair enough. I have two male friends that were lovers 30 years ago – we have been friends through children, divorces, new marriages etc. and I’ve never once considered having sex with either one of them again. It’s been 27 years, my guess is their relationship is something far different than a once a year bone fest.

  13. Amy Bee says:

    Maybe Melinda was turned off by Bill’s role in preventing poorer countries from getting vaccines.

  14. Enis says:

    Sometimes romantic relationships evolve into friendship. One of my best friends is an ex-partner. My husband would have zero issues if we went on a trip together – and we have. It’s been 20 years since we dated, and I see him like family.

  15. lunchcoma says:

    “Irretrievably broken” is just a legal phrase that gets used in divorce filings. The court doesn’t grant a divorce on the grounds of, “Well, we maybe could go to counseling or something, but honestly, we’re pretty tired of each other at this point.”

    Their youngest child is 19. My guess would be that they grew apart over the years, and that now is a good time to make a clean break. There may also be someone else involved. One of the reasons that college age is a good time to split is that people feel more comfortable dating when there aren’t kids with their own opinions at home. I don’t think it’s vacations with the ex, though. Whatever that situation involved, it’s been there the whole time.

    • Rural Juror says:

      This! I don’t see any smoking gun here and it’s weird how people seem to be twisting themselves into pretzels to find some kind of magic reason for their divorce. Sometimes folks decide that they are better off not being married to each other anymore and it’s fine.

      And to everyone raising eyebrows that he would have such a close relationship with another person (ex-gf notwithstanding), I think that we are in many ways socialized to believe that women have close friendships, but men don’t and that’s really damaging. It also leads to many wives doing significant emotional labor supporting their husbands on a daily basis when those husbands view the wives as their “everything” – best friend, therapist, life coach, sexual partner, co-parent, etc. The more we can normalize men having close relationships outside of their marriages or other romantic partnerships, the better of we’ll all be.

      Sorry for the novel.

      • Cava24 says:

        This is so well put-

        I think that we are in many ways socialized to believe that women have close friendships, but men don’t and that’s really damaging. It also leads to many wives doing significant emotional labor supporting their husbands on a daily basis when those husbands view the wives as their “everything” – best friend, therapist, life coach, sexual partner, co-parent, etc. The more we can normalize men having close relationships outside of their marriages or other romantic partnerships, the better of we’ll all be.

        (Just adding that a lot of men don’t reciprocate emotional labor in romantic relationships, the partner is just supposed to give and give.)

    • Veronica S. says:

      To be honest, a lot of times I look at it as…almost thirty years of marriage and three children raised is honestly a success more than it is a failure. Monogamy is a social construct for the most part, and as such, it may not work for everyone in the long run. People change with age. There are lots of reasons why older couples may divorce after children have moved on since they no longer have a shared goal there and may discover they’ve gone different ways emotionally.

  16. Soupie says:

    He’s a tool and Windows 10 sucks too. He also hasno idea how to dress. That photo with the Burgundy sweater…. Ugh. All that money and no smarts about clothing to this day.

    • Anna says:

      Ugh. I just got through trying to use Teams for a new project, and it had me pulling my hair out.

  17. MsIam says:

    I don’t know, that getting the ex’s approval thing reminds me an awful lot of Charles/Camilla/Diana. And we know how that turned out. So we shall see. But maybe Bill is just a prickly pear or maybe she is and now that the kids are grown they are both “done”.

  18. Ania says:

    Theoretically all is cool. But I would be very hurt if my husband had such a close emotional relationship with someone else, let alone his ex.

  19. Amelie says:

    It is very odd, that’s for sure. I looked up this lady, she is one smart cookie and has a brilliant mind from what I can tell. Maybe Bill needed one weekend a year where he could talk genius shop with a like minded person who knew him really well. I find it strange he needed to ask her permission to marry Melinda but then he also did a pros/cons list before he married Melinda which Melinda caught him doing. Ann is married too now. I hope she didn’t ask Bill’s permission to get married.

  20. Maria says:

    This guy is an advocate of vaccine apartheid and has had plenty of shady stuff.
    I don’t get why anyone wants to be so protective of his “privacy”.
    You can have friendships with your ex all you want but asking their permission and go ahead to marry some one else is very Charles/Camilla/Diana. Whatever.

    • emu says:

      That’s true, the permission thing is odd. Maybe it was more getting her honest opinion since she knew him so well.

    • SomeChick says:

      TBH I think it’s the vax apartheid. which has and is continuing to result in mass fatalities. some people just don’t want to be married to satan, ya know?

  21. Lizzie says:

    Neil Simon – Same Time Next Year.

  22. emu says:

    I feel like the weekend with Ann didn’t break the marriage. Honestly, it seems like they are friends but he wanted to make sure Melinda wasn’t jealous because Ann was a woman. Who knows though.

    I am interested to see if any other hot goss comes out though. I feel like Gates has it more together than Bezos or Musk though. I’m sure it’s just an intellectual “uncoupling” where they just don’t need eachother anymore.

  23. Mel says:

    So he’s close with an ex. So what? It’s not drama, it seems to me like it’s adults continuing to adult. Good Lord, people can be friends without having sex.

    • Maria says:

      They *can* but unfortunately usually they don’t, in these kinds of circumstances.

  24. AMJ says:

    I would believe the friendship thing if it weren’t for the “permission”. You don’t ask your friends for a permission to marry someone else. Him asking his ex for it sounds like a mess. Most of us, if placed in Melinda’s position here, would probably run.

  25. Isabella Saxon says:

    This pales beside Bill’s friendship with Jeffrey Epstein. Still, it’s odd that Bill needs to see his ex alone for an entire weekend, as if they’re still a couple. No reciprocation for their spouses. That’s the issue, not that exes can’t get along with new partners. 27 years of this. So Charles and Camilla.

    I would hate it but perhaps Melinda didn’t care. I think Bill is very hard to live with, ala Bezos and Steve Jobs.

  26. Esme says:

    Most of the comments here are assuming she pulled the plug, but I’ve always found her somewhat grating in her public persona, and in some recent clips I’ve seen he looks fed up/embarrassed with her, and for good reason.
    I’ve always seen them as a marriage of convenience (right time for kids, family man image, foundation, money, etc), not as a paring of equals or a great love story.
    The ex gf story is rather cool, imho: he dealt with the situation openly, set boundaries from the beginning, and kept a person he trusted in his life with minimal impact on his marriage – it would love if all adults could be this rational.

    • Crows says:

      Esme, what’s the good reason? She’s very accomplished in her own right?

  27. Mtec says:

    This reminds me of more of a Don and Anna Draper kind of friendship. Or a Richard Gilmore and Pennilyn Lott type of hanging out. (I wish i had real life examples of this lol)

    But if it somehow turned more into a Ewan Mcgregor and MEW situation then I can see how that can make for an “irretrievably broken” situation.

  28. nb says:

    Why is it always that people assume men and women can’t be just friends even if they did have a previous relationship? Is this more of an internal issue, as in “I wouldn’t trust my partner to do that so why would anyone else?” Or is cheating just so ingrained in our culture and marriages that it’s the first thing we think of when we hear of a man and a woman spending time together even if they’re in relationships with other people?

    I’m 36 and I’ve been with my husband for almost 13 years (married for 7). When I take a solo trip to where I grew up I hang out with my male friends from high school, yes a few who I had a brief relationships or flirtations with, and even crash at their places and it’s never sexual. We have grown past that and truly just enjoy each other’s company. It’s comfortable, like being with family. My husband has no problem with it because he knows I’m loyal and have never shown him otherwise. Is it so hard to believe Bill and his friend have the same type of friendship/comfort level?

    • Maria says:

      Did you feel the need to ask the permission of your exes to marry your husband? Kind of a significant difference.

      • A says:

        I feel like people are taking that “permission” thing and running too far with it. What the article says is that he asked her for “approval”, and to me, what it sounds like is that he is friends with her and wants to know what she thinks about this relationship. It sounds like she knows him rather well, and is able to provide some insight into things that he might not be able to see immediately.

        We all have friends, and we all have friends in relationships. Friends have a different vantage point into these things. You see things that your buddies might not really notice right away. I can see certain dynamics in relationships my friends have that they might not be immediately aware of, and I value those takes from them too. If they see something that is concerning or alarming, or if I see something that I find concerning, we tell each other, even as the decision to take that advice is up to the individual. I don’t think asking for what others think that means any of us are giving or withholding permission.

        I get why people think this particular instance of it is weird, and it’s bc he had a relationship with her. I know that’s odd. But it’s not unusual or unheard of for a man to stay friends with a woman after they’ve had a romantic relationship. For a lot of men, that is often the only way they become friends with a woman, and the level of intimacy that is shared in the prior relationship means that they often know the man a lot better than any of his other friends would. Not to mention, Bill Gates isn’t exactly a warm and fuzzy human being who’s got buddies lined up wall to wall. This person seems like the one person in his life who fulfills that role. It’s weird, yes, but it’s not something that really needs to be read into that deeply either, unless there’s other evidence that suggests that he’s actually carrying on an affair with her.

      • Maria says:

        No, I’m sorry A but it still is weird, you can have an emotional attachment to someone you were close to, but if you are calling them to ask their approval or input on whether you should propose to someone (different than asking them input about dynamics while dating), you should be taking a good hard look at your dynamics in the current relationship. There’s too much baggage in a situation like that, and it’s unhealthy. And honestly what you describe about this being the only way many men have female friends and the female ex therefore “knows” the man better than anyone else is still a creepy Charles/Camilla situation.
        If People, an outlet designed to basically be a bunch of press releases, is reporting he asked this woman for approval, it sounds pretty cut and dry.

  29. Crows says:

    I bet the ‘permission’ thing was journalistic licence. He would have discussed it and said, you know me well, what do you think? I remember that story back in the 90s and its oft repeated.

  30. Freddy says:


  31. Leah says:

    So he took yearly vacations with his ex-gf to engage in “intellectual pursuits”. Yeah I could see how his wife would eventually get fed up with that regardless of an arrangement. She married him, not Microsoft 365.

    I always thought they were a stable couple. I remember reading about the scholarship fund they have for low income college bound students.