While some Hollywood A-listers are eager to put their divorce behind them, others still have regrets about their separation.
Kris Jenner, who was married to Robert Kardashian Sr., has previously opened up about having regrets about having an affair with Todd Waterman and ending her relationship with Kardashian Sr., who passed away in 2003 at the age of 59. (The twosome, who shared daughters Kourtney Kardashian, Kim Kardashian, Khloé Kardashian and son Robert Kardashian, were married from 1978 to 1991.)
“He was such a great husband and a such a great dad, and I think that I fell into a situation where I thought that the grass was greener somewhere else, and I made a huge mistake,” Jenner told Khloé on an October 2023 episode of The Kardashians. “That’s my life’s biggest regret.”
Meanwhile, Ben Affleck confessed that his divorce with Jennifer Garner in 2015 was the “biggest regret of his life.” (The pair share three children, Violet, Seraphina and Samuel.)
“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,” he shared in an interview with The New York Times in February 2020. “My drinking, of course, created more marital problems. The biggest regret of my life is this divorce. Shame is really toxic.”
Keep scrolling to see more celebrities who have regrets about getting divorced:
Kris Jenner
Jenner has opened up about regretting cheating on Kardashian Sr. and ending their marriage before his death in 2003. (The twosome were married from 1978 to 1991.)
Although she didn’t get back together with Kardashian Sr., the reality star shared that she and her ex-husband became “best friends” after their divorce prior to his death.
“We talked on the phone all day long, helped each other through things all the time, and I did have regrets,” she explained on an episode of The Kardashians in October 2023. “I thought, ‘Wow, what was I thinking?’”
Samantha Lee
Lee, who was married to Tyrese Gibson from 2017 to 2020, expressed regrets over how they handled their divorce. (The pair share daughter Soraya, born in 2018.)
“I think we do take divorce very casually. I would never tell a woman to walk through that in the same frame as I was when I did it,” she said on the “Hardly Initiated” podcast in October 2023. “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.”
The licensed social worker admitted that she “was not in any position” to make such a big decision as they was “extremely emotionally intoxicated.”
“I would never tell somebody to make that decision when they’re that emotional, but of course, I wasn’t talking to someone that genuinely would be for marriage or for reconciliation,” Lee explained. “That’s no slight to my attorney. At the time when I was on the phone and I made that decision, I was livid. I was emotional. If I’m that emotional and I’m that hurt and I’m on that level, if it’s misguided and misdirected it could go in a bad direction.”
Lee noted that she feels like if she “had different people in [her] ear at the time” she might have made a different decision.
Ben Affleck
Affleck said in a February 2020 interview that the “biggest regret” of his life is his divorce with Garner.
“Shame is really toxic,” he told The New York Times. “There is no positive by-product of shame. It’s just stewing in a toxic, hideous feeling of low self-worth and self-loathing.”
Will Smith
The actor previously noted how his divorce from his first wife Sheree Zampino was really hard for him. (The pair, who share son Trey, were married from 1992 to 1995.)
“With Sheree and with Trey, that was a really difficult time,” he said on an episode of Red Table Talk in June 2020. “Divorce was the worst thing in my adult life, divorce was the ultimate failure for me. 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.”
Lamar Odom
On an episode of The Kardashians in February 2025, the former basketball player reunited with his ex-wife, Khloé. The twosome were married from 2009 to 2016 during which Odom cheated on Khloé and struggled with drug addiction. (In 2015, Odom was found unresponsive after and overdose and Khloé remained by his side during his recovery but continued to precede with the divorce.)
“I have so much to be sorry for, even though I’m not a sorry person,” he told the reality star. “I’m a fighter and I’m a winner. I think some things just break you down and humble the f*** out of you.”
Odom noted he “would be blessed if [he] could find someone even close to” Khloé and the way she “held [him] down.”
“How being around you made me want to be my best self. I wish I could have showed that,” he admitted. “I guess in due time, if you give me the opportunity, you will see I’m genuine and a changed man, and I’m probably cool enough to be your friend.”
Bill Gates
The Microsoft cofounder got candid about separating from Melinda French Gates. The duo tied the knot in 1994 and divorced in 2021. They share kids Jennifer, Rory and Phoebe.
“That was the mistake I most regret,” Bill told The Times in a January 2025 interview referring to his divorce with Melinda. “You would have to put that at the top of the list. There are others but none that matter. The divorce thing was miserable for me and Melinda for at least two years.”
Gavin Rossdale
In January 2017, Rossdale expressed his regrets over his divorce from Gwen Stefani. The duo split in 2015 and share sons Kingston, Zuma and Apollo.
“[Divorce] was completely opposite to what I wanted,” the Bush frontman said in The Sun’s Fabulous magazine interview in January 2017. “Really not … but here we are. Apart from death, I think divorce is one of the hardest, most painful things to go through.”
Shaquille O’Neal
The former basketball player shared that he made “horrible” mistakes in his marriage to Shaunie Henderson. The pair were married from 2002 to 2011 and share sons Shareef and Shaquir and daughters Amirah and Me’arah.
“I was bad. She was awesome,” O’Neal said on “The Pivot Podcast” in April 2022. “It was all me. We don’t need to talk about what I was doing, but I wasn’t protecting her and protecting those vows. Sometimes you live that double life and get caught up. I’m not going to say it was her. It was all me.”
Vicki Gunvalson
The Real Housewives of Orange County star regrets her decision to file for divorce from Donn Gunvalson in 2010 after 16 years of marriage.
“I think Donn was an amazing man, so I’m not going to say he wasn’t good for me,” Vicki said during an appearance on Watch What Happens Live With Andy Cohen in November 2015. “I think that if I had to do it all over again, I would not have divorced Donn. I know that for a fact. We both went sideways for multiple reasons, but hindsight, if we could do things differently, he was a great man, great husband.”
