When Hollywood stars get married, it’s a spectacle of glitz and glamour, and we often imagine their lives as perfect fairytales. But when the marriage ends and divorce becomes public, there’s a human side to these stories that we rarely get to see, going beyond the tabloid headlines.
Despite their fame and fortune, celebrities experience the same heartaches and regrets as anyone else when it comes to relationships. They fall in love, endure heartbreak, and sometimes make choices they later wish they could undo, proving that emotional pain is a universal experience, even under the brightest spotlights.
So, prepare for a trip down memory lane, because we’re breaking down the surprising confessions from A-listers who’ve openly admitted they had major second thoughts about ending their marriages. From tech billionaires to reality TV royalty, these stars have revealed that despite moving on, a part of them wishes things had turned out differently. Grab your favorite snack, because this is going to be a fascinating ride through Hollywood’s most heartfelt divorce regrets.
1. Bill Gates
Starting off our list is a name synonymous with innovation and immense wealth, Bill Gates. In 2021, the world watched as he and Melinda French Gates announced their split after a remarkable 27 years of marriage. It was a partnership that not only built a family with three incredible children but also established one of the world’s most influential philanthropic foundations, working tirelessly to enable people globally to lead healthy, productive lives.
Reflecting on his past, Bill candidly shared with The Times of London that he considers their divorce “the mistake I most regret,” describing the separation as “miserable” for both him and Melinda for at least two years, highlighting that even for the incredibly wealthy, emotional turmoil is a shared human experience.
Despite the undeniable pain and the ultimate ending of their romantic partnership, Bill also offered a perspective filled with gratitude and acceptance. He reflected on the entirety of their shared life, 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.” This sentiment highlights that the immense value he placed on their family and shared endeavors far outweighed the eventual heartache.
He continued to share his current outlook, expressing a sense of moving forward. “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…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.” It’s a powerful testament to finding peace and purpose even after significant personal turmoil, acknowledging the past without dwelling on it excessively.
2. Ben Affleck
Next up, we have Ben Affleck, an A-lister whose personal life has often been as scrutinized as his blockbuster roles. While he has since found love again, back in 2020, Ben was remarkably open about the profound impact of his divorce from Jennifer Garner. The former couple, who share three children, officially split in 2015 and finalized their divorce several years later, marking the end of a Hollywood power couple era.
In a candid conversation with The New York Times, Ben confessed that “the biggest regret of my life is [the] divorce,” a statement that resonated deeply, revealing the profound emotional impact and the difficult feelings of shame he associated with the split.
He eloquently described the destructive nature of shame, explaining, “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 a raw insight into the mental struggles that can accompany a public marital breakdown, showing that celebrity status doesn’t exempt anyone from these challenging emotions.
Ben also spoke about the importance of moving past his mistakes, rather than obsessing over them. “It’s not particularly healthy for me to obsess over the failures — the relapses — and beat myself up. 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,” he shared. It’s a powerful message about resilience and growth, even when facing your deepest regrets.
Their relationship had its ups and downs, with Affleck’s complicated family history taking a toll on him, and he openly discussed his struggles with alcoholism. Despite the challenges, Jennifer Garner has maintained a healthy relationship with her ex-husband, even stating, “When our kids get married, we’ll dance, I know that now. We’ll boogaloo and have a great time. I don’t worry about that anymore.” This speaks volumes about the capacity for forgiveness and co-parenting after immense regret.
3. Vicki Gunvalson
From the glitzy world of Hollywood to the equally dramatic realm of reality television, we turn our attention to Vicki Gunvalson, a familiar face from *Real Housewives*. Vicki was married to her husband, Donn Gunvalson, for a significant 16 years before they ultimately filed for divorce in 2010. Their journey, often documented for public consumption, took a turn that Vicki now openly reflects upon with a sense of regret.
When asked about her past relationship on *Watch What Happens Live*, Vicki admitted that if she had a chance to relive her life, she would not have divorced Donn, stating, “I think Donn was an amazing man… I think that if I had to do it all over again, I would not have divorced Donn. I know that for a fact.”
Her admission offers a rare glimpse into the complex emotions that often follow a divorce, especially when both parties were, at their core, good people. Vicki acknowledged that the responsibility for their split wasn’t entirely one-sided, stating, “We both went sideways for multiple reasons.” This level of self-awareness and shared accountability is truly commendable.
Ultimately, her reflection circled back to the fundamental appreciation she still holds for Donn as a partner. “But hindsight, if we could do things differently, he was a great man, great husband,” Vicki shared. It’s a poignant reminder that even after a marriage ends, the respect and understanding for a former spouse can linger, alongside the bittersweet feeling of ‘what if.’
4. Gavin Rossdale
Next on our list is Gavin Rossdale, the frontman of Bush, whose highly public split from Gwen Stefani in 2015 became a major talking point. Their divorce came amidst swirling rumors that Gavin had cheated with the family’s nanny, adding another layer of complexity and heartache to an already difficult situation. When reflecting on how things unfolded, Gavin expressed a deep sense of regret about the turn their relationship took.
In an interview with The Sun in 2017, Gavin was incredibly candid about his feelings, stating that the divorce was “completely opposite to what I wanted.” This reveals a profound disappointment and a desire for a different outcome, highlighting that even when a relationship publicly unravels, the personal wishes for its longevity can remain strong. He went on to describe the immense difficulty of the experience.
He underscored the severity of the emotional pain, asserting, “Really not…but here we are. Apart from death, I think divorce is one of the hardest, most painful things to go through.” This powerful comparison emphasizes the devastating impact divorce can have, equating it to one of life’s most profound losses. It’s a sentiment many can relate to, regardless of their celebrity status.
Gavin also touched upon the inherent human tendency to harbor regrets, especially after significant life events. He explained, “I know we all wish [things were different], but we can’t, so I have to deal with reality. You can’t not have regrets and be human at the same time.” This acknowledgment of regret as a natural part of the human experience offers a comforting perspective, reminding us that it’s okay to look back and wish for a different path.
5. Samantha Lee
Rounding out our first section is Samantha Lee, who was married to actor and singer Tyrese Gibson for three years before their decision to split in 2020. Her reflection on their divorce offers a unique and incredibly honest perspective, focusing less on the relationship itself and more on the circumstances and emotional state under which the separation decision was made. It’s a powerful lesson in making life-altering choices when you’re not in the right headspace.
Looking back, Samantha described making the decision about her divorce when she was “extremely emotionally intoxicated,” a powerful image that suggests intense emotional upheaval may have clouded her judgment, a sentiment many can relate to after difficult breakups.
Furthermore, Samantha pointed to the influence of those around her during that vulnerable period. She admitted that she only talked through things with her attorney, who she now believes “does not have her best interests in mind.” This regret highlights the critical importance of having supportive and objective counsel when navigating such sensitive personal matters, especially when emotions are running high.
She explained her conviction that she might have made a completely different choice if she “had different people in [her] ear at the time.” This speaks volumes about how external advice and emotional support can sway monumental life decisions. It’s a poignant reminder of the impact our support systems, or lack thereof, can have during times of crisis.
Samantha vividly recalled the raw emotion surrounding her decision, sharing on the *Hardly Initiated* podcast, “I was very, very hurt, I was very angry. I remember when I made the decision I was hysterically crying on the phone with my attorney.” Her account paints a clear picture of a decision made under duress, further reinforcing her belief that such choices should ideally be made with a calm and clear mind, not in the throes of intense pain and anger.
Okay, folks, buckle up because we’re not done with the feels just yet! After our journey through some truly candid confessions, we’re peeling back more layers of Hollywood’s heartaches. It’s time to uncover even more raw emotions from stars who’ve publicly pondered the ‘what ifs’ of their past marriages. Get ready to connect with these incredibly human stories, because let’s be real, regret is a universal language.
6. Kris Jenner
Next up, let’s talk about the original momager, Kris Jenner, who has opened up about her own past regrets. Long before the Kardashian-Jenner empire took over our screens, Kris was married to the late Robert Kardashian, a powerhouse attorney. Their marriage lasted for decades, and they welcomed four children together, laying the foundation for the famous family we know today. But even in their seemingly opulent life, things weren’t always as they appeared.
Kris has openly admitted that her affair with professional soccer player Todd Waterman was the catalyst for their breakup, leading to their divorce in 1991. She’s been incredibly candid about the experience, even writing in her memoir that the affair “made me feel young, attractive, y, and alive,” but also brought a “wave of nausea” as she realized what she was risking. This raw honesty about her conflicting emotions is something many can understand.
Kris shared on the *InCharge With DVF* podcast that one of her “biggest regrets” was her affair, which “broke up my family,” expressing deep sorrow for the choices that ended her marriage and impacted her children, a burden that clearly weighed heavily on her.
She has frequently spoken about Robert through the years, sharing that she still wishes she could pick up the phone and call him. While the regret for her actions is evident, Kris has also found a sense of peace. During a 2023 episode of *The Kardashians*, she told Khloé that she takes solace in the idea that “everything happens for a reason,” suggesting that without that period of her life, Kendall and Kylie Jenner might not be here today. It’s a powerful reflection on accepting the past while embracing the present.
7. Lamar Odom
Remember the whirlwind romance between Khloé Kardashian and Lamar Odom? It felt like a fairytale, albeit a fast-paced one, when they tied the knot just a month after meeting in 2009. They even had their own reality show, *Khloé & Lamar*, giving us an inside look at their lives. But beneath the surface, Lamar has since revealed, their marriage was grappling with some pretty heavy issues that ultimately led to their split in 2013.
Lamar has been incredibly open about the struggles he put Khloé through, particularly his issues with infidelity and substance abuse. In a candid interview on *TMZ Presents: Lamar Odom: Sex, Drugs & Kardashians*, he admitted, “Behind the scenes, I put her through s—. Like, s— that y’all don’t know.” He also confessed to having “full-blown relationships” while playing in the NBA, painting a clear picture of the betrayal that eroded their marriage. These are the kinds of truths that often only come out years later.
Despite the pain and public scrutiny, Lamar has expressed profound regret about their divorce. During an appearance on *Celebrity Big Brother*, when Cynthia Bailey commented that their divorce “sounds like one of your biggest regrets,” Lamar didn’t hesitate with his response: “Yes, it is.” It’s a powerful moment when a celebrity, often seen as larger than life, admits to such a deep personal regret on national television, making him incredibly relatable.
Even after their split and his near-fatal drug overdose, Khloé’s unwavering support for Lamar highlights an enduring connection and respect that transcends heartbreak, serving as a poignant reminder that lessons learned and hope for personal growth can emerge even from painful endings.
8. Courteney Cox
Rounding out our list of A-listers with divorce regrets is none other than Courteney Cox, who found love with David Arquette while starring in the iconic *Scream* franchise. Their on-screen chemistry spilled over into real life, leading to marriage in 1999 and the arrival of their daughter, Coco, in 2004. They were a beloved Hollywood couple for over a decade, navigating the ups and downs of life in the spotlight together.
Courteney and David were always open about working on their marriage, even attending therapy to address their challenges. As Courteney once told *InStyle*, “We’re not lazy about our marriage. We have the same arguments we’ve had for years.” This level of commitment to trying to make things work truly shows how much they valued their relationship, highlighting that even with effort, some hurdles can be insurmountable.
Despite their dedication, the couple eventually split in a trial separation in 2010, ultimately filing for divorce in 2012. Looking back, Courteney admitted to *More* magazine, “In divorce you always have regrets.” It’s a candid and universally understood statement, acknowledging that even when a split feels necessary, there’s almost always a part of you that wishes things could have gone differently, or that you could have prevented the outcome.
David Arquette echoed similar sentiments, telling *The Guardian* that his biggest regret related to their divorce was its impact on their daughter, Coco, stating, “My daughter, Coco, because divorce is so difficult,” a heartfelt admission from both parents that underscores the profound and lasting effect marital endings have on children.
From tech moguls to reality stars and movie icons, these A-listers demonstrate that regret transcends fame and fortune, reminding us that in matters of the heart, we all navigate love, mistakes, and the desire to turn back time, proving that vulnerability and reflection are truly universal human experiences.
