10 Celebrities Who Regret Getting Divorced

10 Celebs Who Regret Getting Divorced
Freelancer Notes: Ive used quotes from the celebrities and mentioned the outlets where they stated them, and used these as the main basis of the entries.
Welcome to MsMojo, and today were looking at the celebrities who got candid about their marital breakdowns.
#10: Jennifer Aniston
During the aughts, youd have to be living under a rock to miss the Brad and Jen media frenzy. With Brangelina taking over headlines, the world watched Anistons marriage crumble in the tabloids. Even two decades later, fans still wonder what happened. In a 2005 interview with Vanity Fair, Aniston offered a peek behind the curtain, admitting, Theres a lot I would probably do differently. She elaborated that taking time off their careers to be together may have strengthened their relationship. Brad Pitt reportedly carries some measure of regret as well. According to Us Weekly, the actor wishes hed handled the end of their marriage in a more thoughtful manner.
#9: Robin Thicke
Just as Thickes career skyrocketed with the smash hit Blurred Lines, his marriage to Paula Patton hit rock bottom. To his credit, the singer took most of the blame, making a series of grand overtures to win her back. In addition to naming his next album after her and recording a heartfelt ballad, he even asked fans to ask Patton to give him another chance. Unfortunately, none of his grand gestures worked, and the pair filed for divorce in 2014. In an interview with People Magazine, Thicke admitted, It was a melting pot of trouble brewing, and I was so arrogant that I thought I could handle it all.
#8: Bill Gates
For decades, Bill and Melinda Gates marriage seemed built to last, which made their divorce all the more shocking. Their split was met with widespread public interest, as private details of their union spilled out. Just when the buzz had since simmered down, Bill made headlines again in January 2025. In an interview with The Times of London, he reflected on the miserable divorce, calling it the mistake I regret the most. His choice of words wasnt the most careful, with some misinterpreting it as regret over the marriage itself. Gates clarified on NBCs Today show, saying that even if I knew that it wouldn't last forever, I would still do it again.
#7: Courteney Cox
Much like their Scream characters, Courteney Cox and David Arquettes chemistry was undeniable. Tying the knot in 1999, the couple stayed together for over a decade before their 2010 separation, officially divorcing three years later. According to Cox, the breakup of their relationship wasnt due to a lack of effort. In an interview with More magazine, the actress explained, In divorce you always have regret. We were married for a long time, so it's not like we didn't try. Although details behind their split remain private, Cox and Arquette have maintained a healthy friendship, with the actress calling Arquette her very best friend.
#6: Shaquille ONeal
By his own admission, the former basketball superstar had it all in his marriage with Shaunie Nelson. The pair, married from 2002 to 2011, faced numerous ups and downs before calling it quits. In his 2011 autobiography, Shaq Uncut: My Story, ONeal takes full blame for their marital woes, admitting to his infidelity. Years later, speaking on The Pivot Podcast, the athlete called himself greedy, claiming It was all me during their marriage. Admitting he didnt fully value family life when he had it, ONeal has expressed regret at letting it all slip away. While owning up to his mistakes on The Big Podcast, he called his time with Shaunie and his children the happiest days of my life.
#5: Gavin Rossdale
The Bush frontman and Hollaback Girl singer kept their marriage intact for over a decade before announcing their separation in 2015. In her divorce filing, Stefani cited Rossdales alleged affair with their childrens nanny as a key factor. Things took a bitter turn before their divorce was finalized the following year. Speaking on the Amy & T.J. podcast, Rossdale called their separation the simple shame in my life. He also described the effect it had on their children as debilitating, regretting the impact the split had on them. To avoid repeating past mistakes, the singer takes extra care not to speak negatively about his ex, hoping to protect their children from further disappointment.
#4: Ryan Phillippe
Among the hottest young couples of their time, Ryan Phillippe and Reese Witherspoons relationship dominated tabloids, convincing many that they were in it for the long haul. But it wasnt to be. In 2006, the Cruel Intentions co-stars announced their separation, initiating divorce proceedings that lasted for the next two years. In an interview with W magazine, Phillippe looked back at this period with mixed feelings, referring to it as the worst time in my life. The actor recalled isolating himself in his house for days to avoid paparazzi, calling it a disturbing environment for his then-8-year-old daughter. While he has since moved past it, the media spotlight hovering over his and Witherspoons separation left a lasting mark.
#3: Kris Jenner
Though shes now mainly known as Kris Jenner, there was a time when she was Kris Kardashian. Her marriage to Robert Kardashian, which lasted from 1978 to 1991, was complicated by her affair with Todd Waterman. In an episode of The Kardashians, Kris opened up about her past indiscretion. Ashamed of the mistakes made in her youth, the socialite remembered her former husband fondly, calling him a great husband and great dad. The pair mended their friendship before his death in 2003. Still, Kris has taken responsibility for her actions, considering the infidelity that ended her marriage as her lifes biggest regret.
#2: Will Smith
Before his name was forever entangled with Jada Pinkett, Will Smith was first married to Sheree Zampino. The marriage lasted three years, during which Zampino gave birth to Smiths first son, Trey. Although Will moved on with Jada, the breakdown of his first marriage continues to haunt him. In an episode of Pinkett Smiths Red Table Talk series, the actor revealed that divorce was the ultimate failure for me. Separating from the mother of his then 2-year-old child hit him hard, and Smith still considers it the worst thing in my adult life. To add insult to injury, Zampino filed for divorce on Valentines Day.
#1: Ben Affleck
From the aughts to the mid-2010s, Ben Affleck and Jennifer Garner were among Hollywoods iconic It couples. For a decade, their marriage was seen as a benchmark for success, until the pair announced their separation in 2015. Afflecks life took a steep downturn soon after, with his troubles frequently highlighted in the press. Years later, the actor opened up about his past struggles, which stemmed from his alcohol use disorder. Speaking to The New York Times, Affleck viewed the end of his marriage with Garner as The biggest regret of my life, adding that Shame is really toxic. He echoed these statements in another interview with The Sydney Morning Herald, labeling the divorce as a very painful experience.
Which failed Hollywood marriage lives rent-free in your mind? Let us know in the comments.
