Discover the stories behind why these famous individuals wish they had chosen a different path from divorce.

In 2021, the tech magnate Bill Gates and his long-time spouse Melinda made headlines when they announced their separation after 27 years of marriage. Reflecting on their relationship and the life they built together, Bill revealed in an interview with The Times of London that their divorce is “the mistake I regret the most.” He candidly shared that the emotional turmoil following their separation was “depressing” for both of them, lasting for at least two years, although he has started to find peace with it.

“Despite the divorce being quite challenging, the joys of raising our three children and the meaningful work we accomplished together still stand out. Even knowing it [the marriage] wouldn’t last forever, I would willingly choose to do it all over again,” he shared during an appearance on the Today Show.

Bill continued, “Though my career has had its ups and downs, overall, it has been incredibly rewarding. My children are doing wonderfully too. It’s hard for me to complain about anything at this point. I’ve moved on from the divorce, and Melinda seems to be thriving. I’m engrossed in my work, which I love, so I have no real complaints.”

Ben Affleck may have moved on from his marriage to Jennifer Garner, but in a candid moment in 2020, he expressed that “the greatest regret of my life is the divorce.” The former couple, who share three children together, ended their marriage in 2015, finalizing their divorce a few years later. While he acknowledged feeling a sense of shame about the split, he emphasized that dwelling on that feeling was not beneficial.

“Shame is really toxic,” he commented during an interview with The New York Times. “There’s no positive outcome that comes from feeling ashamed; it only breeds a toxic, hideous cycle of low self-esteem and self-hatred.”

He further elaborated, “It’s not healthy for me to obsess over failures — the relapses — and to continually berate myself. I have made mistakes, and I genuinely regret some of my actions. However, it’s essential to pick yourself up, learn from your experiences, and strive to move forward.”

The Real Housewives star Vicki Gunvalson was married to her husband Donn Gunvalson for 16 years before they decided to file for divorce in 2010. Upon reflecting on their separation, Vicki admitted that if given the chance to redo everything, she would not have chosen to divorce Donn.

“I believe Donn was an incredible man, and I won’t say he wasn’t good for me. If I had the option to do it all again, I would not have divorced Donn. I know that for a fact. Although we both faced challenges for various reasons, in hindsight, if we could have navigated things differently, he was a great man and an excellent husband,” Vicki shared on Watch What Happens Live.

After Gavin Rossdale separated from Gwen Stefani in 2015, he voiced his regrets about how their relationship unfolded. Their divorce was marred by rumors of infidelity on Gavin’s part, involving the family’s nanny, and he openly expressed that he “clearly wished things had turned out differently.”

“The outcome I faced was completely opposite to what I had envisioned,” he stated in an interview with The Sun in 2017. “Honestly, I never expected this, but here we are. I believe that aside from death, divorce is one of the hardest and most painful experiences one can endure.”

He added, “I know we all desire to avoid regrets, but life doesn’t always allow that, so I must face the reality of my situation. It’s impossible to be human and not have regrets.”

Samantha Lee was married to actor Tyrese Gibson for three years before they made the difficult decision to separate in 2020. Upon reflection, she revealed that she made the choice during a time when she was “extremely emotionally intoxicated” and primarily communicated her feelings through her lawyer, who she felt did not have her best interests at heart. She expressed that she believes her decision might have been different if she had consulted with more supportive individuals during that period.

“I was incredibly hurt and very angry. I remember when I made the decision, I was hysterically crying on the phone with my lawyer,” she recounted on the Hardly Initiated podcast.

She continued, “I would never advise anyone to make such a significant decision while in a heightened emotional state, but unfortunately, at that moment, I wasn’t talking to someone who genuinely supported marriage or reconciliation. This isn’t a criticism of my lawyer; rather, in that moment of anger and pain, the decision I made felt misguided and could have led to negative outcomes.”

Before fame and his marriage to Jada Pinkett Smith, actor Will Smith was previously married to Sheree Zampino, the mother of his oldest son, Trey. Upon reflection, Will has described his first marriage as one of his greatest failures and a significant regret in his life.

“Looking back at my relationship with Sheree and my son Trey, it was an incredibly challenging period,” he shared on Red Table Talk. “Divorce was the most painful experience of my adult life, and it felt like the ultimate failure. I’ve encountered many hardships as an adult, but nothing compares to the pain of divorcing my son’s mother when he was just two years old.”

Kris Jenner and her late husband Robert Kardashian divorced many years ago, but she continues to express regret over their separation, which was partly triggered by her affair. Over the years, Kris has frequently shared fond memories of Robert, often wishing she could reach out to him again.

“I got married when I was very young,” she reflected on the InCharge With DVF podcast. “I met Robert when I was just 18. We dated for four years and married at 22. At one point in my life during my 30s, I had an affair, and my greatest regret is that it ultimately destroyed my family.”

Larsa Pippen acknowledges that her family is in a much better place now that she and ex-husband Scottie Pippen have separated, yet she admits to having deep regrets about their divorce. Reflecting on her life in 2022, she expressed a desire to have kept her family intact.

“I wish my children could have had the experience of growing up with both a mother and father in the same household. I feel a deep sense of guilt because I grew up with my parents together,” Larsa shared with Us Weekly. “I wanted my children to have that same experience, but as for our relationship, I can honestly say that it’s better than it’s ever been. We truly care for each other and support one another. Our relationship is in a great place now, and we continue to prioritize our children’s well-being.”