Bill Gates, Kris Jenner, Will Smith — And 7 Other Celebs Who've Said They Regret Getting Divorced

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04-05-2025

Like marriage, divorce is not a decision to be taken lightly. While there are examples of couples reconciling (and even remarrying) after a split, those stories are few and far between. Often, after a marriage ends — especially in the public eye — the "bridges" between a couple are far too burnt to ever recross...
After the initial turmoil, some individuals, whether famous or not, ultimately regret ending their marriage. Many celebrities have been outspoken about the reasons why they regret their divorces, and even their roles in the unraveling of previous relationships. So, without further ado, here are 10 celebrities who publicly admitted their divorce regrets:
1. Kris Jenner:
The marriage: As Kris recounted during a 2022 episode of The Martha Stewart Podcast, she first met Robert Kardashian at a horse race in California, "I met him when I was 17, almost 18. I met him at the Del Mar race track, and I was there with some friends — I wasn't old enough to place a bet, so I had to stand over to the side of the people, the betting window. My friends were betting, and I would give them my $3, and they would place a bet for me. He came up to me and introduced himself, and that's how we met."
She added that she and Robert, who was 11 years her senior, "dated and eventually got engaged."
By 1978, the couple married and Kris became pregnant with their eldest daughter, Kourtney, on their honeymoon. The Jenner-Kardashian matriarch said this resulted in a wave of backlash from Robert's conservative Armenian family: 'I got pregnant on our honeymoon. I had Kourtney nine months, two weeks, and two days later. And I know that because all the Armenian ladies were probably counting. So I was like, 'No, I promise I got pregnant on my honeymoon!' You know, those were the days that [I was] very old-fashioned."
Within the next eight years, the couple welcomed three other children — Kim, Khloé, and Rob.
The divorce: In 1989, Kris began an affair with professional soccer player-turned-animator Todd Waterman. In her 2011 autobiography, the now-69-year-old wrote, "That kiss [between her and Waterman] was more than amazing; it was like a revival, a resuscitation, an awakening from some long, deep, unconscious sleep...It made me feel young, attractive, sexy, and alive. Along with these feelings came a wave of nausea. I actually wanted to throw up at the same time. Because it dawned on me that I had not felt that way with Robert for years."
After Kris confessed to the affair, she and Robert divorced in 1991.
The regret: Jenner described the divorce as one of the "biggest regrets" of her life. Writing, "I had lost Robert. Suddenly, I realized everything that was great about my marriage. Robert was the greatest guy in the world. He would never cheat on me. He only wanted the best for me."
However, in 2023, the famous "momager," sat down with daughter Khloé during T he Kardashians, to discuss her past infidelities and stated that she takes solace in the idea that everything works out the way it's supposed to: "I'm not proud of the way that I behaved during that time, but you know what? Everything happens for a reason. I really do live my life by thinking God has a plan, and without that whole thing happening, there never would've been Kendall and Kylie." (Kris married now-ex Caitlyn Jenner one month after her divorce was finalized).
2. Will Smith:
The marriage: During a 2018 episode of Red Table Talk, the now 56-year-old revealed he met his first wife, Sheree Zampino, in 1991 on the set of A Different World — although he initially visited the sitcom in hopes of meeting Jada: "The dude that was going to introduce me to Jada was with another girl and I was like 'Who is that?' I went to Different World to meet Jada, and met Sheree and ended up marrying Sheree and having [my son] Trey with Sheree."
The regret: In the 2020 Father's Day episode of Red Table Talk, the "Gettin' Jiggy Wit It" singer sat down with host (and wife) Jada Pinkett-Smith to discuss their co-parenting journey with Zampino (who was also present during the interview).
Pinkett-Smith began, "I want to talk about one interesting concept that you've brought up quite a bit in regards to Trey and divorce — and the idea being that just because a man might not be the best husband, does not mean he isn't a good father."
"With Sheree and with Trey, that was a really difficult time. Divorce was the worst thing in my adult life, divorce was the ultimate failure for me," the Bad Boys star responded. "I've been hurt a lot in my adult life. But I don't think anything touches the failure of getting divorced from my 2-year-old son's mother."
3. Bill Gates:
The marriage: Bill and Melinda French Gates met in 1987 when she took a job in product development at Microsoft. However, their meeting wasn't love at first sight; in the 2019 docuseries, Inside Bill's Brain: Decoding Bill Gates, Bill revealed, "When we first met, she had other boyfriends, and I had Microsoft."
However, by 1993, it was publicly confirmed that the couple was engaged when they were spotted sharing a soda during a Seattle Sonics game.
The pair married in a private ceremony on New Year's Day 1994. They went to great lengths to keep the ceremony intimate, even booking the empty rooms in their hotel and hiring every helicopter on the island to keep the paparazzi at bay.
Within eight years, the couple welcomed their children: Jennifer, Rory, and Phoebe.
The divorce: In May 2021, the tech power couple announced they were splitting in a joint statement on X: "After a great deal of thought and a lot of work on our relationship, we have made the decision to end our marriage. We have raised three incredible children and built a foundation that works all over the world to enable all people to lead healthy, productive lives. We continue to share a belief in that mission and will continue our work together at the foundation, but we no longer believe we can grow together as a couple in this next phase of our lives."
The divorce was finalized on August 2, 2021. Although the full financial details of the settlement have never been revealed, it was noted that Melinda was allocated over $2 million in stocks and shares.
After exiting her co-chair position at the Bill & Melinda Gates Foundation, now simply known as the Gates Foundation, the 60-year-old wrote in a statement on X: "Under the terms of my agreement with Bill, in leaving the foundation, I will have an additional $12.5 billion to commit to my work on behalf of women and families."
The regret: In January 2025, while promoting his autobiography, Source Code: My Beginnings, Gates told the Times of London that his divorce was "at the top of the list" of his failures in life and "the divorce thing was miserable for me and Melinda for at least two years."
A few weeks later, during an appearance on the Today show, Gates addressed his prior comments, stating, "Despite the fact that the divorce wasn't great, having those three kids, the work we were able to do together — even if I knew that it [wouldn't] last forever, I would still do it again. My business career, though, there's been some up and downs, has been incredibly phenomenal. My kids are phenomenal. So it's even hard for me to complain about things."
Ultimately, Gates said, "I've moved past the divorce, and Melinda's doing well. I've got a lot of work that I love to do. So I'm not really complaining about anything."
4. Ben Affleck:
The marriage: Affleck and Jennifer Garner first met in 2000 on the set of the war film Pearl Harbor, in which Affleck starred as Captain Rafe McCawley, and Garner had a small part as a nurse named Sandra. However, during the couple's initial meeting, Garner was married to Felicity co-star Scott Foley.
The duo reunited once again on the set of Daredevil in 2003, but at that time, Garner and Foley were still married, and Affleck had recently gotten engaged to Jennifer Lopez. Garner and Affleck still became good friends, with the 13 Going On 30 star telling People, "He's your basic tall, dark and handsome. He's it. I can't imagine anyone in the world I would rather see swoop in and save the day than Ben."
Garner filed for divorce from Foley in April 2003, and Affleck and Lopez ended their engagement in January 2004. By October of that year, Garner and Affleck took their romance public by appearing at Games 1 and 2 of the 2004 World Series to cheer on Affleck's home team, the Boston Red Sox. In a 2010 interview with Parade, Garner revealed that her and Affleck's romance began over email, "Well, it helped that we were both single at the time," she said. "He's a very good writer...He's a very persuasive writer."
In June 2009, the couple had a private wedding ceremony in Turks and Caicos. Affleck and Garner's reps confirmed they were married and expecting their first child. Garner later told InStyle, "We were able to have a beautiful, private wedding and I couldn't be happier."
The divorce: Days after their tenth anniversary, Garner and Affleck announced they were divorcing: "After much thought and careful consideration, we have made the difficult decision to divorce. We go forward with love and friendship for one another and a commitment to co-parenting our children whose privacy we ask to be respected during this difficult time. This will be our only comment on this private, family matter. Thank you for understanding."
In March 2017, Affleck completed rehab and thanked Garner for her support on Facebook, "I have completed treatment for alcohol addiction; something I've dealt with in the past and will continue to confront. I want to live life to the fullest and be the best father I can be. I want my kids to know there is no shame in getting help when you need it, and to be a source of strength for anyone out there who needs help but is afraid to take the first step. I'm lucky to have the love of my family and friends, including my co-parent, Jen, who has supported me and cared for our kids as I've done the work I set out to do. This was the first of many steps being taken towards a positive recovery."
The following month, he and Garner officially filed for divorce, which was finalized on October 5, 2018.
The regret: In 2020, Affleck opened up to the New York Times about how his divorce and alcohol misuse were related, "I drank relatively normally for a long time. What happened was that I started drinking more and more when my marriage was falling apart. This was 2015, 2016. My drinking, of course, created more marital problems."
"The biggest regret of my life is this divorce." The Armageddon star continued, "Shame is really toxic. There is no positive byproduct of shame. It's just stewing in a toxic, hideous feeling of low self-worth and self-loathing. It's not particularly healthy for me to obsess over the failures — the relapses — and beat myself up.
He admitted that he ultimately used the experience as a learning opportunity, "I have certainly made mistakes. I have certainly done things that I regret. But you've got to pick yourself up, learn from it, learn some more, try to move forward."
5. Courteney Cox:
The marriage: During an 2009 interview, David Arquette recalled that he and Cox first met at a pre-filming party for Scream,"I was being a little cocky and Courteney was like, 'Ah, I've heard of you,' and we just kept flirting for a while. She's just so gorgeous and she jokes around so much."
He said it was love at first sight for him, but not for Cox, adding, "I had to trick her." However, in 2011, Cox told Robin Roberts that she and Arquette "fell in love on the first" movie.
By September 1998, the couple became engaged during a beach vacation with Cox's family. Director Wes Craven recalled Arquette waited until fireworks began, got down on one knee, and asked, ​​"Courteney Cox Arquette, will you marry me?" The pair were married the following June in San Francisco and welcomed daughter Coco in June 2004.
The divorce: In October 2010, the couple announced they were undergoing a "trial separation" period with a joint statement: "We remain best friends and responsible parents to our daughter and we still love each other deeply. As we go through this process we are determined to use kindness and understanding to get through this together."
Arquette's rep confirmed that the actor had entered a rehab program three months later. Cox released a statement of support, telling People,"I really admire David and his choice to take charge and better his life." She added, "I love and support him."
A month later, Arquette checked out after completing his treatment and visited the Oprah Winfrey Show a few weeks later, where he spoke about the state of his marriage, 'I want her [Cox] to be happy. If me being the best person I can be doesn't make her happy in a partner, in who she needs, whatever she's looking for, that's still to be answered.' He added that he didn't know if a happy ending was possible, but that he'd 'love for it to work out.'
However, the couple officially filed for divorce on June 8, 2012, which was finalized the following May.
The regret: The following year, Cox told More, "When you love someone, you want them to be happy, even if it's not with you."
The Friends star noted that she and Arquette both had fought for their marriage, but at the end of the day, it simply wasn't enough, "You can love somebody so much, but it's not the life you should be living together. I think David and I are supposed to be the way we are now." She continued, "In divorce you always have regrets. We were married for a long time, so it's not like we [didn't] try."
6. Shaquille O'Neal:
The marriage: Shortly after moving from Florida to California in 1996 to join the Los Angeles Lakers, Shaq met film marketer and future wife, Shaunie Nelson.
In January of 2000, the couple welcomed their first child (both Shaq and Shaunie had children from previous relationships), Shareef Rashaun. The following November, Shaunie gave birth to their daughter, Amirah Sanaa.
The following year, the pair wed in a top-secret ceremony at the Beverly Hills Hotel. Details about the wedding were kept under wraps, even from the 248 guests, until the last second. Fellow Lake Brian Shaw later revealed, "Since we didn't find out until the last minute what was going on, I didn't know it was black tie."
The secrecy apparently paid off because Shaq's mother, Lucille, called the wedding "the event of a lifetime."
Over the next four years, the couple welcomed two more children, son Shaqir Rashaun and daughter Me'arah Sanaa.
The divorce: In September 2007, Shaq filed for divorce in Miami. The petition from his lawyer stated: "The marriage between the parties is irretrievably broken."
However, by the following August, the couple had called off the divorce, with Shaunie telling the Associated Press, "Neither one of us could probably answer why we were getting one in the first place. Things have been going so great, that someone actually had to remind us that 'Hey, you do remember those papers are still there.' Literally, it was days ago." The Basketball Wives creator added, "So, we've agreed that before we leave Florida we'll make sure that that's gone away."
But by 2009, their marriage was on the rocks again, this time Shaunie filed for separation, citing irreconcilable differences and seeking full custody of their children. A year later, the couple reached a settlement.
The regret: In his 2011 memoir, Shaq Uncut: My Story, the NBA Hall of Famer first expressed regret for the way he handled his marriage and admitted to infidelity, as well as not being the "best partner."
He wrote, "At one time my ex-wife Shaunie and I were happy, but I admit it — I was a guy. I was a guy with too many options. Choosing to be with some of those women, well, that's on me. In my mind, I never did it disrespectfully, but obviously I shouldn't have done it all."
The athlete added: "You know as well as I do relationships are about maintaining ... It wasn't the big stuff, it was the small stuff, and that's my fault. I had things to do. I was trying to win, trying to make some money. I admit I wasn't the best partner. I just didn't know how. I'm learning now."
In her 2024 memoir, Undefeated: Changing the Rules and Winning on My Own Terms, Henderson wrote of her ex's infidelities, "Looking back, I don't know that I was ever really in love with the man," she wrote. "I was in love with the idea of being married to the man I had a family with. I was in love with the idea of building a life together."
The day after the book's release, Shaq took to Instagram in a post many commenters deemed "mature," writing: 'I understand...I wouldn't have been in love with me either. Wishing you all the best...All love, Shaq.' He captioned the post, 'Trust me i get it."
7. Gavin Rossdale:
The marriage: Rossdale and Gwen Stefani first crossed paths in 1995 while their bands (Bush and No Doubt) were performing at a concert for an LA radio station.
On New Year's Day 2002, after six years of long-distance dating, Rossdale proposed to Stefani. Eight months later, the couple married in a 17th-century church in London with only 150 guests before hosting another ceremony for Stefani's family in California.
Over the next 12 years, the couple welcomed their sons: Kingston, Zuma, and Apollo.
The divorce: In August 2015, the couple unexpectedly announced their divorce with a joint statement: "While the two of us have come to the mutual decision that we will no longer be partners in marriage, we remain partners in parenthood and are committed to jointly raising our three sons in a happy and healthy environment."
The regret: During a March 2024 interview on Amy Robach and T.J. Holmes's podcast, Amy & T.J., Rossdale revealed that his "clearest, simplest shame" was giving his sons a "broken home."
NBC / NBCU Photo Bank/NBCUniversal via Getty Images
"I feel bad for my kids, that's it." The now-59-year-old continued, "I wish I could have found a way to not have that in their lives. It wasn't fun for me to come from a broken home. It can be quite debilitating for kids…the overriding things is you don't want to let your kids down. The biggest thing would be when you see the kids, that sometimes there's a loss. It'd be nice if there was more of a connection with the person who made them with me."
Despite describing his and the "Hollaback Girl" singer's divorce as a "very contentious, hugely emotional, flared-up situation," Rossdale claimed that he tries not to speak negatively about his ex. "Less said, soonest mended, and I said nothing. I'm handcuffed because I would never want to overly say anything negative about their mom. That's just not right."
8. Ryan Phillippe:
Rebecca Sapp / Getty Images for SBIFF
The marriage: Philippe and ex Reese Witherspoon first crossed paths in March 1997. During an interview with Jane magazine the following year, the Legally Blonde star claimed they met at her 21st birthday party. "I don't know what came over me — maybe the seven Midori sours — but I told him, 'I think you're my birthday present.' He thought it was so flattering and now that I think about it…how embarrassing!"
Stephane Cardinale - Corbis / Sygma via Getty Images
While many believed that the stars met and fell for each other while filming Cruel Intentions, Witherspoon set the record straight during a 2015 Watch What Happens Live! appearance, stating that the pair had already been "living together for about a year and a half" during the movie's production.
The couple became engaged in 1998 and married in June 1999 in Charleston, South Carolina. At their wedding, Witherspoon was several months pregnant with daughter Ava. They welcomed son Deacon in October 2003.
The divorce: On October 30, 2006, the couple announced they were going their separate ways in a joint statement through their rep: "We are saddened to announce that Reese and Ryan have decided to formally separate. They remain committed to their family and we ask that you please respect their privacy and the safety of their children at this time."
Witherspoon officially filed for divorce on November 8, 2006, citing "irreconcilable differences." The divorce was finalized on October 5, 2007, with final arrangements settled the following June. The exes were granted joint custody of their children.
The regret: In February 2008, Philippe opened up to W magazine and claimed his divorce was "the darkest, saddest place I've ever been."
Michael Loccisano / FilmMagic
"There were a good four or five months of not being able to get out of bed. It was the worst time of my life." He continued, "You get through it. It's a process that's not easy, but I get less and less sad about it every day."
The then-33-year-old also addressed the claims that an affair was behind his marriage unraveling. He stated the real reason was "far more complicated and far less interesting than it's made out to be. To look and search for these salacious reasons, to pin it on a person, or a moment in someone's life, it's not realistic."
9. Vicki Gunvalson:
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The marriage: Real Housewives of Orange County stars Vicki and Don Gunvalson married in 1994 and founded Coto Insurance and Financial Services the same year.
Bravo / Bravo/NBCUniversal via Getty Images
In RHOC's premiere episode on March 21, 2006, Donn described his then-wife as "a very I-am-woman-hear-me-roar, you know, get-out-of-my-way kind of gal." Throughout the reality show's early seasons, these personality differences were shown to increase their marital tension.
In 2009, the couple renewed their vows at the Grace Bay Resort in Turks and Caicos. Vicki later wrote on her blog, "When Donn read me the vows he wrote, I was so happy. Hearing how he respects me and loves me is worth everything to me. He loves me for who I am and isn't looking for me to make changes to make him happy."
The divorce: However, by October 2010, Vicki filed for divorce. At the time she told People, "Donn has been an important part of my life and he will continue to be. Anyone who has gone through a divorce understands that this is a personal matter and a difficult time in our lives. It's amicable and we are not at odds with one another. It's just time."
In the June 2011 RHOC reunion episode, Donn told his side of the story to host Andy Cohen, "I found out that Vicki filed for divorce when the process server showed up at my office. From the get-go, the time I was asking Vicki to give me and our time together just didn't happen." He continued, "Every evening, she was working late, and her trips would become longer, and she'd call less and less. It was typical Vicki — she orchestrated [the divorce], that's how she rolls."
"Vicki should feel bad she hurt me. What she did was not cool in anybody's eyes. A marriage and a man should be treated with dignity. I don't think how this went down was treated with class or dignity and I deserve both," he concluded.
The regret: At BravoCon 2022, during the "Right the Relationship" panel, Vicki recalled her "biggest regret" was divorcing Donn, telling the audience, "I divorced my husband for Brooks [Ayers] and it's the biggest regret I ever had...I will never, ever cheat again. It destroyed my family."
Gunvalson and Ayers broke up in August 2015 after she claimed that he had duped her by stating he had been diagnosed with cancer. In November 2015, Ayers admitted to falsifying documents about his cancer treatment, but not the diagnosis itself.
Since 2022, Gunvalson has been dating entrepreneur Michael Smith.