Celebrities Who Wish They Hadn’t Divorced

While some Hollywood A-listers are keen to move on from their divorces, others continue to experience regret regarding their separations.

Kris Jenner, who was married to Robert Kardashian Sr., has openly discussed her regrets about having an affair with Todd Waterman and ending her marriage with Kardashian Sr., who sadly passed away in 2003 at the age of 59. (The couple, who had daughters Kourtney Kardashian, Kim Kardashian, Khloé Kardashian, and son Robert Kardashian, were wed from 1978 to 1991.)

“He was an incredible husband and father, and I think I fell into a trap where I believed the grass was greener elsewhere, and I made a grave mistake,” Jenner confided to Khloé during an October 2023 episode of The Kardashians. “That’s my greatest regret in life.”

In a similar vein, Ben Affleck admitted that his divorce from Jennifer Garner in 2015 remains the “biggest regret” of his life. (The couple shares three children: Violet, Seraphina, and Samuel.)

“I drank relatively normally for a long time. The reality is that I started drinking more heavily as my marriage fell apart. This was around 2015 and 2016,” he explained in a February 2020 interview with The New York Times. “My drinking led to more marital issues. The biggest regret of my life is this divorce. Shame is profoundly toxic.”

Keep reading to discover more celebrities who have expressed regrets about their divorces:

Kris Jenner

Jenner has revealed her feelings of regret over having cheated on Kardashian Sr. and the end of their marriage before his passing in 2003. (The couple was married from 1978 to 1991.)

Despite not rekindling their romance, the reality star noted that she and her ex-husband became “best friends” post-divorce.

“We would talk on the phone all day, supporting one another through tough times, and I truly had regrets,” she recounted on an episode of The Kardashians in October 2023. “I thought, ‘What was I even thinking?’”

Samantha Lee

Lee, who was married to Tyrese Gibson from 2017 to 2020, voiced her regrets regarding how their divorce was handled. (The couple shares a daughter, Soraya, born in 2018.)

“I believe we often take divorce too lightly. I would never encourage a woman to navigate it in the same mindset as I was when I went through it,” she shared on the “Hardly Initiated” podcast in October 2023. “I was deeply hurt and very angry. I recall making that decision while crying hysterically on the phone with my attorney.”

As a licensed social worker, she noted that she “was not in any state” to make such a significant choice as she was “extremely emotionally overwhelmed.”

“I would advise against making such decisions when highly emotional; however, I was not consulting with someone genuinely interested in marriage or reconciliation,” Lee clarified. “This isn’t a slight to my attorney, but at that moment, I was furious and emotional. Being in such an emotional state can lead to misguided and poor decisions.”

She expressed that if she “had different voices in [her] ear at that time,” she might have made a different choice.

Ben Affleck

Affleck mentioned in a February 2020 interview that the “biggest regret” of his life is his divorce from Garner.

“Shame is profoundly toxic,” he expressed to The New York Times. “There is nothing redeeming about shame. It merely festers in a toxic, horrible state of low self-worth and self-hatred.”

Will Smith

The actor has previously discussed the difficulty of his divorce from his first wife Sheree Zampino. (The couple, who shares son Trey, was married from 1992 to 1995.)

“With Sheree and Trey, that was an exceptionally challenging period,” he stated on an episode of Red Table Talk in June 2020. “Divorce was the worst experience of my adult life; it felt like the ultimate failure. I’ve faced various challenges as an adult, but nothing compares to the failure of divorcing my son’s mother.”

Lamar Odom

During a February 2025 episode of The Kardashians, the former basketball player reconnected with his ex-wife, Khloé. The two were married from 2009 to 2016, during which Odom faced issues with drug addiction and infidelity. (In 2015, he was found unresponsive due to an overdose, and Khloé stayed by his side throughout his recovery but still chose to move forward with the divorce.)

“I have much to be remorseful for, even though I’m not inherently a sorry person,” he told the reality star. “I’m a fighter and I’m a winner. Sometimes, experiences break you down and truly humble you.”

Odom expressed that he would be grateful if he could find someone even nearly as wonderful as Khloé and appreciated how she “supported” him.

“Being around you inspired me to become my best self. I regret not demonstrating that,” he confessed. “If given the chance, I hope to prove that I’m genuine and transformed, and perhaps I could be your friend.”

Bill Gates

The Microsoft co-founder candidly discussed his separation from Melinda French Gates. The couple wed in 1994 and divorced in 2021, sharing children Jennifer, Rory, and Phoebe.

“That is the mistake I most regret,” Bill shared in a January 2025 interview with The Times, reflecting on his divorce from Melinda. “I would rank that at the very top of the list. There are other mistakes, but none that hold significance. The divorce brought misery to both me and Melinda for at least two years.”

Gavin Rossdale

In January 2017, Rossdale shared his regrets about his divorce from Gwen Stefani. The couple split in 2015 and has three sons: Kingston, Zuma, and Apollo.

“[Divorce] was entirely contrary to what I wanted,” the Bush frontman expressed in an interview with The Sun’s Fabulous magazine in January 2017. “It wasn’t what I desired at all… but here we are. Aside from death, I believe divorce is one of the hardest, most painful experiences to endure.”

Shaquille O’Neal

The former basketball player admitted that he made “terrible” errors during his marriage to Shaunie Henderson. The couple was married from 2002 to 2011 and shares sons Shareef and Shaquir and daughters Amirah and Me’arah.

“I was wrong. She was incredible,” O’Neal confessed on “The Pivot Podcast” in April 2022. “It was entirely my fault. We don’t need to delve into my actions, but I failed to protect her and uphold our vows. At times, one can lead a double life and get caught up. I won’t place the blame on her; it was all on 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 believe Donn was a fantastic man, so I can’t say he wasn’t good for me,” Vicki stated during an appearance on Watch What Happens Live With Andy Cohen in November 2015. “If I had a second chance, I would not have divorced Donn. I am certain of that. We both faced challenges for many reasons, but in hindsight, if changes could be made differently, he was a great man and a wonderful husband.”