Celebrities reveal their biggest relationship regrets

Madonna recently answered 50 fan questions on her YouTube channel to promote her new album, 'Finally Enough Love.' One fan asked the singer to reveal a decision she made in the past that she now feels wasn't the best. Madonna answered, "Getting married. Both times." The Queen of Pop has been married twice, first to Sean Penn from 1985 and 1989, and then to director Guy Ritchie from 2000 to 20008.

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Madonna -

In regards to her marriage to Ritchie, the singer said, "I stepped into a soap opera, and I lived in it for quite a long period of my life." Not a great review! Sean Penn is a more complicated figure in her life. Madonna has publicly showered him with praise and expressed her love for him in the decades since their divorce, even jokingly offering to re-marry him. They seem to be on excellent terms, despite rumors of physical abuse within their marriage.

Madonna says that while her marriages were perhaps not her best ideas, she has zero doubts about her family, saying that her six children are her proudest achievements.

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Lamar Odom -

Lamar Odom seems to regret his past behavior with Khloé Kardashian more every day. The former basketball star opened up about his ex in a sneak peek of 'Celebrity Big Brother,' in which he's seen speaking to fellow houseguest Todrick Hall.

"I dreamt [about] my ex-wife last night," Odom says, and when Hall asks who he's referring to, and how many ex-wives he has, the NBA alum replies, "Just the one and only."

When Hall realizes he's talking about Kardashian, he asks if the two still talk, and Odom says, "No, I miss her so much." He then admits, "I wish I could take that time back." This wasn't the first time Odom has expressed his regret.

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Jay-Z - On cheating on Beyoncé, Jay-Z said, "The hardest thing is seeing the pain on someone's face that you caused, and then have to deal with yourself."

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Brad Pitt - The heartthrob regrets how his relationship with Jennifer Aniston came to an end. Pitt confessed that their marriage could have ended in a "more thoughtful manner.”

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Jada Pinkett Smith - The actress's biggest relationship regret is dating Will Smith while he was still married.

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Kristen Stewart - The actress regrets cheating on then-boyfriend Robert Pattinson with director Rupert Sanders.

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Jennifer Lopez - J.Lo said her failed marriage with ex-husband Marc Anthony was the biggest disappointment of her life.

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Ben Affleck -

In April 2020, the actor opened up about his divorce from Jennifer Garner. "The biggest regret of my life is this divorce. Shame is really toxic," he shared.

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Kim Kardashian - Kim Kardashian once said that her biggest relationship regret was not dating Kanye West sooner. That answer has likely changed since then!

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Jude Law - The actor regrets cheating on Sienna Miller with his children's nanny.

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Gwyneth Paltrow - The actress regrets screwing up so many relationships.

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Britney Spears - The pop star regrets her marriage to dancer Kevin Federline.

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Melissa Joan Hart - She regrets not dating her 'Sabrina the Teenage Witch' film co-star Ryan Reynolds.

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Michael Douglas - The veteran actor shared how he regrets taking Catherine Zeta-Jones for granted after their temporary split.

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Courteney Cox - "In divorce you always have regret," the actress said about her divorce from David Arquette.

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Amanda Seyfried - The actress doesn't seem to be able to get over her ex Dominic Cooper.

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Hugh Grant - The actor was caught cheating on Liz Hurley with a prostitute and deeply regrets it.

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Burt Reynolds - The late actor never really got over Sally Field. He told Vanity Fair she was the love of his life.

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Aaron Carter - He deeply regrets losing Hilary Duff, whom he has called "the love of his life."

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Nicole Kidman - Kidman marvels at how young she was when she married Tom Cruise. The actress was 23.

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Calvin Harris - The DJ regrets taking on Twitter when he and Taylor Swift broke up.

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Robin Thicke - The singer apologized numerous times to Paula Patton for his alleged cheating, but to no avail.

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Ozzy Osbourne - The Prince of Darkness regrets cheating on his wife, Sharon Osbourne.

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Mila Kunis - The actress regrets how she handled her breakup with Macaulay Culkin.

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Kris Jenner - "The one regret, if I had to do it over, would be divorcing Robert Kardashian," she told New You magazine.

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James Franco - James Franco regrets not taking his girlfriend to the hospital when his cat scratched her eye. The actor was busy with work, so he sent his assistant instead.

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John Stamos - Lori Loughlin "could be the one that got away" for the actor.

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Ben McKenzie - The actor wishes he had listened more in his relationships.

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Nick Viall - Nick Viall of 'The Bachelor' regrets revealing on national television that he slept with Andi Dorfman.

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Jef Holm -

Jef Holm regrets breaking up with Bachelorette Emily Maynard.

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Getty Images

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Madonna -

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Madonna -

Madonna says that while her marriages were perhaps not her best ideas, she has zero doubts about her family, saying that her six children are her proudest achievements.

Getty Images

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Lamar Odom -

"I dreamt [about] my ex-wife last night," Odom says, and when Hall asks who he's referring to, and how many ex-wives he has, the NBA alum replies, "Just the one and only."

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Jay-Z - On cheating on Beyoncé, Jay-Z said, "The hardest thing is seeing the pain on someone's face that you caused, and then have to deal with yourself."

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Brad Pitt - The heartthrob regrets how his relationship with Jennifer Aniston came to an end. Pitt confessed that their marriage could have ended in a "more thoughtful manner.”

5 / 32 Fotos

Jada Pinkett Smith - The actress's biggest relationship regret is dating Will Smith while he was still married.

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Kristen Stewart - The actress regrets cheating on then-boyfriend Robert Pattinson with director Rupert Sanders.

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Jennifer Lopez - J.Lo said her failed marriage with ex-husband Marc Anthony was the biggest disappointment of her life.

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Ben Affleck -

In April 2020, the actor opened up about his divorce from Jennifer Garner. "The biggest regret of my life is this divorce. Shame is really toxic," he shared.

Getty Images

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Kim Kardashian - Kim Kardashian once said that her biggest relationship regret was not dating Kanye West sooner. That answer has likely changed since then!

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Jude Law - The actor regrets cheating on Sienna Miller with his children's nanny.

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Gwyneth Paltrow - The actress regrets screwing up so many relationships.

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Britney Spears - The pop star regrets her marriage to dancer Kevin Federline.

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Melissa Joan Hart - She regrets not dating her 'Sabrina the Teenage Witch' film co-star Ryan Reynolds.

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Michael Douglas - The veteran actor shared how he regrets taking Catherine Zeta-Jones for granted after their temporary split.

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Courteney Cox - "In divorce you always have regret," the actress said about her divorce from David Arquette.

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Amanda Seyfried - The actress doesn't seem to be able to get over her ex Dominic Cooper.

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Hugh Grant - The actor was caught cheating on Liz Hurley with a prostitute and deeply regrets it.

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Burt Reynolds - The late actor never really got over Sally Field. He told Vanity Fair she was the love of his life.

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Aaron Carter - He deeply regrets losing Hilary Duff, whom he has called "the love of his life."

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Nicole Kidman - Kidman marvels at how young she was when she married Tom Cruise. The actress was 23.

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Calvin Harris - The DJ regrets taking on Twitter when he and Taylor Swift broke up.

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Robin Thicke - The singer apologized numerous times to Paula Patton for his alleged cheating, but to no avail.

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Ozzy Osbourne - The Prince of Darkness regrets cheating on his wife, Sharon Osbourne.

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Mila Kunis - The actress regrets how she handled her breakup with Macaulay Culkin.

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Kris Jenner - "The one regret, if I had to do it over, would be divorcing Robert Kardashian," she told New You magazine.

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James Franco - James Franco regrets not taking his girlfriend to the hospital when his cat scratched her eye. The actor was busy with work, so he sent his assistant instead.

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John Stamos - Lori Loughlin "could be the one that got away" for the actor.

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Ben McKenzie - The actor wishes he had listened more in his relationships.

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Nick Viall - Nick Viall of 'The Bachelor' regrets revealing on national television that he slept with Andi Dorfman.

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Jef Holm -

Jef Holm regrets breaking up with Bachelorette Emily Maynard.

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Celebrities reveal their biggest relationship regrets

Madonna reflects on her two marriages, saying they weren't her best ideas!

09/06/23 | StarsInsider

CELEBRITY Relationships

Regrets—we all have them. There's always something we wish we would have done differently. When it comes to relationships, these regrets can haunt us for some time, but we can also learn from our mistakes and use them as a catalyst for change, for better relationships in the future.

Celebrities also have their breakups and makeups, and even they regret some things they've said or done in the past. Whether they let that special someone get away, or ended up cheating, there are many famous people who still regret their actions to this day.

Browse through the gallery and get to know your favorite stars' relationship regrets.