Hailey Watson
Celebrity Relationship Regrets That Might Surprise You
Stars seem to have it all—fame, fortune, and fairytale romances.
But even celebrities make mistakes in love that they later wish they could take back.
From cheating scandals to choosing the wrong partner, these famous faces have opened up about their biggest relationship regrets, and some of their confessions might just catch you off guard.
1. Kris Jenner’s Affair Ended Her Marriage to Robert Kardashian
Kris Jenner has been honest about one of her biggest mistakes: cheating on Robert Kardashian Sr. with a man named Todd Waterman.
During a 2023 episode of The Kardashians, she tearfully admitted that Robert was an amazing husband and father.
She confessed that she thought life would be better with someone else, but she was completely wrong.
Her affair destroyed her marriage and left her with lasting guilt.
Looking back, Kris realizes she had something special with Robert and wishes she had appreciated it more.
Her story reminds us that sometimes we don’t value what we have until it’s gone.
2. Ben Affleck Calls Divorce from Jennifer Garner His Biggest Regret
Ben Affleck doesn’t hold back when talking about his failed marriage to Jennifer Garner.
In a 2020 interview with The New York Times, he called their divorce the biggest regret of his entire life.
He talked openly about the shame he felt after their split, admitting that shame can be really damaging to a person.
Ben struggled with personal issues during their marriage, including problems with alcohol.
Even though they’ve both moved on, Ben has made it clear that losing Jennifer and hurting his family weighs heavily on him.
His honesty shows that even Hollywood A-listers deal with deep emotional pain.
3. Will Smith Viewed His First Divorce as Ultimate Failure
Will Smith has always seemed like the perfect guy, but his first marriage to Sheree Zampino ended in heartbreak.
On a 2020 episode of Red Table Talk, Will admitted that divorce was the worst thing that ever happened to him as an adult.
He called it his ultimate failure, showing just how much it affected him emotionally.
Will had high expectations for himself and felt like he had let everyone down.
Despite building a successful life with Jada Pinkett Smith afterward, the pain from his first divorce never fully disappeared.
His vulnerability reminds us that everyone carries past wounds, no matter how successful they become.
4. Bill Gates Regrets Ending His Marriage to Melinda
When Bill Gates and Melinda French Gates announced their divorce in 2021, the world was shocked.
Bill later opened up about his deep regret over their split in a 2025 interview.
He admitted that ending his marriage was the mistake he regrets most in life, putting it at the very top of his list.
Their divorce came after reports of Bill’s questionable behavior and connections to Jeffrey Epstein.
Bill’s public admission shows that even billionaires can’t buy back lost relationships.
His words highlight how important it is to treat the people we love with respect and honesty before it’s too late.
5. Gavin Rossdale Didn’t Want to Divorce Gwen Stefani
Gavin Rossdale’s split from Gwen Stefani wasn’t his choice, and he’s made that clear in interviews.
In 2017, he admitted that their divorce was the complete opposite of what he wanted for their family.
He seemed heartbroken when he said those words, showing that he still cared deeply about Gwen.
Their marriage ended after reports of Gavin’s infidelity with their nanny.
Despite the mistakes he made, Gavin expressed genuine sadness about losing his wife and the life they built together.
His regret serves as a reminder that our actions have consequences we might not be ready to face.
6. Shaquille O’Neal Admits He Ruined His Marriage
Basketball legend Shaquille O’Neal doesn’t blame anyone but himself for his failed marriage to Shaunie Henderson.
In a brutally honest 2022 interview, Shaq said, “I was bad.
She was awesome.
It was all me.”
He took full responsibility for his mistakes, including being unfaithful during their relationship.
Shaq’s admission is rare in a world where people often make excuses or point fingers.
His honesty about being the problem shows real growth and maturity.
By owning his mistakes publicly, Shaq hopes to inspire others to learn from his failures and treat their partners better.
7. Vicki Gunvalson Wishes She Never Left Donn
Reality TV star Vicki Gunvalson from The Real Housewives of Orange County has openly regretted divorcing Donn Gunvalson.
In a 2015 interview, she called Donn an amazing man who was good for her.
She confessed that if she could go back in time, she would never have divorced him.
Vicki’s career success came at a personal cost, and she realized too late what she had given up.
Her story is a powerful lesson about balancing ambition with personal relationships.
Sometimes the grass isn’t greener on the other side—it’s just different grass with different problems.
8. Jennifer Lopez’s Multiple Marriage Regrets
Jennifer Lopez has been married four times, and she’s admitted to having regrets about some of her choices.
Her first marriage to Ojani Noa lasted less than a year, and she later called it a mistake.
She also rushed into marriage with backup dancer Cris Judd, which ended quickly as well.
J.Lo has said she sometimes married for the wrong reasons or moved too fast.
Despite her romantic mistakes, she’s learned valuable lessons about love and what she truly needs in a partner.
Her journey shows that even when we make mistakes repeatedly, we can still grow and find happiness eventually.
9. Johnny Depp Regrets His Tumultuous Relationship with Amber Heard
Johnny Depp’s relationship with Amber Heard became one of Hollywood’s most controversial and toxic partnerships.
After their messy divorce and legal battles, Johnny has expressed deep regret about ever getting involved with her.
Their relationship was marked by accusations of abuse from both sides, damaging both of their careers and reputations.
Johnny lost major movie roles and faced public scrutiny.
Though he eventually won a defamation case against Amber, the damage to his personal life was already done.
His experience is a stark warning about recognizing red flags early in relationships before things spiral out of control.
10. Kim Kardashian’s 72-Day Marriage to Kris Humphries
Kim Kardashian’s wedding to NBA player Kris Humphries was a massive televised event watched by millions.
But just 72 days later, Kim filed for divorce, making it one of the shortest celebrity marriages ever.
She later admitted that she knew it was a mistake almost immediately but felt pressured to go through with the wedding.
The whole ordeal was embarrassing and hurt both of their reputations.
Kim has said she regrets not trusting her gut instinct before walking down the aisle.
Her story teaches us that it’s better to disappoint people by canceling a wedding than to make a lifelong mistake.
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