13 Celebrities Who Opened Up About Their Biggest Relationship Regrets
Everyone makes mistakes in love, even the rich and famous. Celebrities might seem like they have it all figured out, but they struggle with heartbreak and bad decisions just like the rest of us.
When stars open up about their relationship regrets, they remind us that nobody’s perfect and that we can all learn from our missteps.
1. Kris Jenner’s Affair Confession
Back in the day, Kris Jenner thought the grass was greener on the other side. Her affair with Todd Waterman ended her marriage to Robert Kardashian Sr., and she’s been honest about how much she regrets it.
On a 2023 episode of The Kardashians, she called Robert a great husband and dad. Looking back, she realized she made a huge mistake by thinking someone else could offer her more.
Her honesty shows that even successful people can lose sight of what truly matters.
2. Ben Affleck’s Divorce Heartbreak
If you could ask Ben Affleck about his biggest regret, he’d tell you it’s divorcing Jennifer Garner. The Hollywood actor hasn’t been shy about expressing how much he wishes things had turned out differently.
In a 2020 interview with The New York Times, he said the divorce was the biggest regret of his life. He also talked about how toxic shame can be when you’re dealing with such a painful situation.
His openness reminds us that fame doesn’t protect anyone from heartache.
3. Kim Kardashian’s 72-Day Marriage
Remember when Kim Kardashian married Kris Humphries and the whole thing lasted just 72 days? Yeah, she wishes you’d forget about it too.
That brief marriage became one of the most talked-about celebrity mishaps ever.
During the 2021 Keeping Up with the Kardashians reunion, Kim admitted it’s probably the one thing she wishes didn’t exist. Though she believes everything happens for a reason, this particular chapter still stings.
Sometimes our most public mistakes teach us the most valuable private lessons.
4. Amber Rose’s Kanye West Reflections
Amber Rose has never been one to bite her tongue, especially when it comes to her relationship with Kanye West. She’s been super candid about regretting how things ended between them.
According to her, the way Kanye treated her left her feeling hurt and disrespected. The whole situation taught her important lessons about standing up for herself and recognizing red flags early.
Her willingness to speak out helps other people feel less alone when they’ve been through similar experiences.
5. Demi Moore’s Marriage Compromise
In her memoir Inside Out, Demi Moore got brutally honest about her marriage to Ashton Kutcher. She revealed regretting that she agreed to threesomes during their relationship, trying to prove how fun and cool she could be.
Looking back, she realized she was compromising her own boundaries to keep him happy. That’s a painful realization that many people can relate to, even if the circumstances are different.
Her story is a powerful reminder to never lose yourself trying to please someone else.
6. Jada Pinkett Smith’s Timing Mistake
Jada Pinkett Smith has admitted she regrets getting involved with Will Smith while he was still married to his first wife, Sheree Zampino. Talk about complicated beginnings!
She’s been open about wishing she’d handled things differently.
According to Jada, she should have fallen back and waited until Will’s divorce was completely finalized. Starting a relationship during someone’s marriage creates messy situations that can haunt you later.
Her honesty shows that even decades-long marriages can have rocky starts we wish we could redo.
7. Hugh Grant’s Infidelity Admission
Hugh Grant’s cheating scandal with Elizabeth Hurley became tabloid gold back in the day. However, unlike some celebrities who make excuses, Hugh has owned up to doing a bad thing without trying to justify his behavior.
He’s acknowledged his infidelity and admitted he wouldn’t make excuses for what he did. That level of accountability is refreshing in Hollywood, where spinning stories is pretty common.
Though the relationship ended, his willingness to accept responsibility shows real growth and maturity over the years.
8. Gwyneth Paltrow’s Multiple Mistakes
Gwyneth Paltrow doesn’t do anything halfway, including relationship mistakes! She’s admitted to messing up so many romantic relationships that she’s lost count.
That takes some serious self-awareness to confess publicly.
While she didn’t get super specific about each situation, her general admission shows she’s done a lot of reflecting. Recognizing patterns in your failed relationships is the first step toward building healthier ones.
Her blunt honesty is actually pretty relatable for anyone who’s stumbled through the dating world multiple times.
9. Justin Bieber’s Space Issues
Young love can be intense, and Justin Bieber learned that the hard way with Selena Gomez. He’s reflected on their relationship, admitting they were way too close and didn’t give each other enough breathing room.
According to Justin, the lack of space led to some seriously intense fights between them. When you’re constantly in each other’s faces, even small disagreements can blow up into major drama.
His reflection shows that sometimes loving someone means knowing when to step back and maintain healthy boundaries.
10. Jay-Z’s Infidelity Consequences
When Jay-Z cheated on Beyoncé, the whole world eventually found out through her album Lemonade. He’s since admitted to his infidelity and talked about how painful it was to see the hurt he caused.
According to the rapper, the hardest part was seeing pain on Beyoncé’s face knowing he was responsible for it. Then he had to deal with his own guilt and shame on top of everything.
His admission reminds us that betrayal creates damage that goes way beyond the moment it happens.
11. Demi Lovato’s Learning Experiences
Demi Lovato has been through a lot publicly, including struggles with relationships. She’s expressed regret over various past romantic situations, though she’s kept many details private to protect everyone involved.
What she has shared is that she’s made mistakes and learned valuable lessons from each one. Growth comes from recognizing where you went wrong and making changes moving forward.
Her journey shows that relationship regrets don’t define you—how you grow from them does. That’s wisdom we can all use!
12. Miley Cyrus’s Wrecking Ball Regret
Okay, so this isn’t exactly a relationship regret in the traditional sense, but Miley Cyrus wishes she’d thought twice about that naked wrecking ball music video. The song was about heartbreak, but the video overshadowed everything else.
Miley has said she’ll always be remembered as the naked girl on a wrecking ball, which frustrates her. She wanted people to focus on the emotional message, not just the shocking visuals.
Sometimes the way we express our heartbreak can create its own set of regrets down the road.
13. Robert Pattinson’s Twilight Romance Regret
While this relates more to a fictional relationship, Robert Pattinson has expressed regret about playing Edward Cullen in the Twilight series. He described the experience as too miserable, which affected his real life too.
The intense scrutiny of his on-screen and off-screen romance with Kristen Stewart made everything harder. Being constantly watched and judged took a toll on both the role and his actual relationship.
Sometimes professional choices impact our personal lives in ways we never expected or wanted them to.
