30 Celebrities Reveal Their Biggest Relationship Mistakes

October 08, 2019

It’s no secret that dating can be rough, especially when things don’t end up working out.

Being in a relationship with someone can complicate things almost instantly, and when communication and intimacy isn’t on point, or the right feelings just aren’t there, things can get messy fast.

Everyone has made some sort of dating mistake at least once in his or her lives before (probably a lot more than once, honestly!), and we’ve all done something with a crush or romantic partner that we regret.

That’s even true for celebrities.

It doesn’t matter how much money or fame they have: celebrities can make mistakes just like the rest of us. Some stars have even opened up about their more personal regrets, like the ones about their relationships.

You’ll probably be surprised to find out that you can actually relate to some of their biggest relationship mistakes – maybe you’ve even made a few of them yourself.

1. Calvin Harris

When DJ Calvin Harris and Taylor Swift broke up a few years ago, things got a little awkward on social media. Harris ended up tweeting a bunch of angry messages towards Swift that everyone could read.

In a 2017 interview with GQ, Harris admitted that he regretted tweeting about Swift.

He said, “It was completely the wrong instinct. I was protecting what I see as my one talent in the world being belittled. It felt like things were piling on top of me and that was when I snapped.”

He also said that he only responded so publicly because he felt pressure from how much attention was on their relationship.

He explained, “Now I see that Twitter thing as a result of me succumbing to pressure. It took me a minute to realize that none of that matters. I’m a positive guy. For both of us it was the wrong situation. It clearly wasn’t right, so it ended.”

2. Justin Bieber

After Justin Bieber’s on-again/off-again relationship finally ended for real (we think,) Bieber admitted the relationship mistake that led to things ultimately not working out.

Bieber told Complex that the two were a little too close to make things work.

He explained, “My full identity was in her. Her identity was in me. When stuff would happen, I would lose my freakin’ mind, and she would lose her mind, and we would fight so hard because we were so invested in each other.”

It sounds like he regrets that they didn’t give each other enough space, which makes sense.

3. Jay Z

For years, there have been rumors that Jay Z has cheated on Beyonce, which seemed even more true after she released Lemonade.

In an interview with the New York Times, the rapper admitted that he had been unfaithful, and expressed what a mistake it was.

Jay Z said, “The hardest thing is seeing pain on someone’s face that you caused, and then have to deal with yourself. So, you know, most people don’t want to do that. You don’t want to look inside yourself.” Luckily, the power couple has worked things out and gotten back together since.

4. Demi Moore

Demi Moore has been revealing a lot about her past relationship with Ashton Kutcher in her upcoming memoir, Inside Out.

One notable thing she said is that she wishes she never had threesomes with Kutcher.

Moore said that they had two threesomes together, and she only agreed to take part in them because she wanted to make Kutcher happy.

She says she regrets the “mistake,” saying, “I wanted to show him how great and fun I could be.”

5. Jada Pinkett Smith

Jada Pinkett Smith and Will Smith started seeing each other when Will was still married to his first wife, Sheree Fletcher.

Jada has since expressed her regret about dating Will when he was in a relationship with someone else.

In an episode on her Facebook show Red Table Talk, she sat down with Fletcher and admitted, “Because I did not understand marriage, I did not understand divorce, I probably should have fell back.”

6. Hugh Grant

The British actor famously got arrested after being caught with a prostitute while dating Elizabeth Hurley.

He later talked about the mistake, saying he had done the wrong thing.

During a 1995 appearance on The Tonight Show with Jay Leno, Grant ‘fessed up to his mistakes, saying, “You know in life what’s a good thing to do and a bad thing to do. I did a bad thing,”

He also wouldn’t make excuses for his behavior.

He went on to say, “People have given me tons of ideas on this one, from ‘I was under a lot of pressure, I was lonely, I fell down the stairs when I was a kid’ . . . but I think it would just be bollocks to say anything like that.”

7. Melissa Joan Hart

Melissa Joan Hart hasn’t admitted to a mistake she made in a relationship, but has instead admitted to a mistake she made by not dating someone.

In an interview, Hart said she kind of wished she had dated Ryan Reynolds when she had the chance.

The two were costars in the 1996 TV movie Sabrina the Teenage Witch, and apparently almost dated officially. She told Australia’s Studio 10 talk show, “We were smitten and cute. He was adorable. He was a really nice guy.” She explained that they didn’t date because she was with someone else, saying, “[He] probably would have been a great boyfriend. And I didn’t end up with the other guy, so maybe I should have taken a chance!”

8. Whitney Port

The reality star is another celebrity who regrets missing the opportunity to date a fellow celebrity.

In an episode of her podcast, With Whit, Whitney Port said she almost hooked up with Leonardo DiCaprio, and wishes she did.

Port said that the two met at a party and exchanged numbers. He later invited her back to his house, but she said no. She said, “I was nervous. I had never had a one-night stand.” She explained that she “didn’t want to be with him alone … I was way too nervous to do it and then I lost my chance and it’s really one of my bigger regrets in life.”

9. Nicole Kidman

If Nicole Kidman could turn back time, she probably wouldn’t marry Tom Cruise… or at least she wouldn’t have at the age she was.

Kidman has famously said that she made the mistake of getting married much too young (she was 23 at the time she married Cruise).

In an interview with the U.K.’s Red magazine, she said, “I was so young when I got married. I look back now and I’m like, ‘What?’” She added, “You look at Taylor Swift, I mean how old is she? She’s 26. I had two kids by the time I was 27 and I’d been married for four years. But that’s what I wanted.”

10. James Franco

Apparently, James Franco hasn’t always been the best boyfriend, and he feels badly about the mistakes he’s made.

He once said he regrets having his assistant take an ex-girlfriend to the hospital instead of going with her.

Franco told Variety, “There was one instance, this old girlfriend was visiting me in New York. I had come out here for school. My cat had scratched her in the eye. I had so much work to get done for the next day, I didn’t take her to the hospital. I had my assistant take her. That moment haunted me so much. What kind of selfish, self-centered boyfriend are you?”

11. John Stamos

The Full House star kind of wishes that he dated one of his co-stars.

Stamos is another one who made the mistake of letting a celebrity get away. He has said he wishes he dated Lori Loughlin.

When speaking with Huffington Post Live, Stamos said that the two went on one date: “We went on a date to Disneyland before we were both married. In real life, when we were 18, 19 years old. No disrespect to her family and her husband now, I would say that she could be the one that got away. She’s one of my dearest friends, and that’s good enough. I really do adore her.”

So it’s not all bad!

12. Britney Spears

Who could forget when Britney Spears was married to her backup dancer Kevin Federline?

The singer has since said that she made a mistake by marrying Federline.

In her documentary For The Record, Spears said that she married Federline “for the wrong reasons,” adding, “Instead of following my heart and doing something that made me really happy, I just did it for the idea of everything.”

That is such a relatable feeling.

13. Milo Ventimiglia

Milo Ventimiglia has actually said that he made a mistake by dating one of his exes.

In an interview, Ventimiglia said he regrets dating ex-girlfriend Hayden Paettiere, his Heroes co-star.

When asked what he learned from the relationship, which was intensely followed by the media, he said, “Never do it again.” Ouch!

Ventimiglia went on to explain that he’s still glad the experience made him who he is today.

He wisely added, “There are things that happen to you in your life that shape who you are. Everything I’ve been through from jobs to friendships to partnerships, everything has built me to who I am. You learn from it. You learn a better way of doing things. It wasn’t until my mid to late ’20s that the job wears on you, relationships wear on you. But I wouldn’t change a thing. When you get knocked over the head in life, it builds your perspective.”

14. Ben McKenzie

The actor has actually said that he made a mistake in the way that he treated some of his exes.

Not everyone can admit they’ve acted the wrong way as a significant other, but Ben McKenzie did in an interview.

When speaking with Elle, McKenzie said that he wishes he had listened to his ex-girlfriends more. He explained, “It’s a bit of a cliché, but basically I wish I’d listened more. Get over your ego a bit. Listen to a different perspective and you almost always modify your position and realize you’re probably too dogmatic, too competitive, too jealous, too frustrated. I love women for being able to knock that s— out of you.”

15. Awkafina

Awkafina has opened up about her relationship mistakes in the past.

The star said that she had made the mistake of changing herself to please her partner because of her own insecurities.

Awkafina went on to explain that she acted like a different person around one ex-boyfriend, saying, “So then there became two me’s. There became like the real me and this other weird me that pretended to have read Infinite Jest. It wasn’t me. And I remember thinking maybe I would have to negotiate these identities, which me would come out, because my friends definitely know that I’m not into brutalist architecture.”

Fortunately, things didn’t last.

16. Emma Thompson

Emma Thompson is another star who regrets not dating someone… kind of.

Thompson has said that she could have gone on a date with Donald Trump, but didn’t.

In an interview with Vanity Fair, Thompson said that Trump asked her out to dinner once, but she turned him down. She said, “Now, of course, it is a source of amusement and kind of existential despair. Because I could have done something.” You just don’t know, do you? I could have changed things. One way or the other.” Who knows!

17. Jenny Slate

Sometimes, celebrities don’t regret something they did in a relationship, but they regret a mistake they made in making it public.

Take Jenny Slate, for example: she wishes she didn’t speak so openly about her breakup with ex-boyfriend Chris Evans.

After the two broke up, Slate did a very honest interview about it with New York Magazine. In a later interview with Marie Claire, she admitted she wished she hadn’t gotten quite so deep, saying, “It goes through all these other outlets and gets distilled. And then it can be made to seem like you were being cheap. I didn’t mean to do that. Especially not with an experience that was so precious to me.”

18. Kris Jenner

Sometimes you end things with someone, and you end up realizing it was a huge mistake. Kris Jenner can relate!

The reality star mogul revealed in an interview that she wishes she never divorced Robert Kardashian.

She told Daily Mail’s New You magazine, “The one regret, if I had to do it over, would be divorcing Robert Kardashian. But then there wouldn’t have been Kendall and Kylie, so that’s the way I look at that. I don’t have a lot of regrets.”

At least there’s always a silver lining!

19. Katie Couric

The news anchor turned down a date with a pop legend, and still regrets that mistake to this day.

Who was it? None other than Michael Jackson.

Couric once told Jimmy Kimmel that Michael Jackson had asked her out, but she said no. She explained, “Can you imagine going home to my daughters who were then about 8 and 4, saying, ‘Honey, Girls. I’m going out on a date with Michael Jackson.’ I just thought it would be too weird. The tabloids would go crazy and I didn’t need that.”

Later, she talked about it again with Howard Stern and admitted she wished she had said yes.

She said, “I do regret not having dinner with him. That would have been insane – breaking bread with Michael Jackson!”

20. Kim Kardashian

Kim Kardashian and Kanye West had a flirty relationship for a long time before they finally officially got together.

Kardashian’s only regret? That they didn’t do so sooner.

She once told Glamour, “I went through so many mistakes that must have hurt Kanye, watching me get married, knowing, that’s not the right situation for you. So it was a great feeling when I was finally like, ‘OK, this is’. My only regret is that I didn’t give it s shot sooner. It would have saved so much BS. I feel like I got the fairytale.”

21. John Mayer

Two years after John got a little too candid during an interview with Playboy magazine, about Jessica Simpson and Jennifer Aniston, he apologized and wished he could take the TMI comments back.

In the interview he compared sex with Simpson to “crack cocaine” and revealed he had “never really gotten over” his split with Aniston.

I was going through a time in my life where I didn’t really want to share what was going on, but I didn’t want to be boring,” he told NPR.

22. Gwyneth Paltrow

While being interviewed by Girlboss Radio’s Sophia Amoruso, the actress got really honest when asked about relationship regrets.

“Oh my God. I’ve f—ked up so many relationships, so many,” she confessed.

“I’m actually a pretty good friend and a good sister and a daughter and a mother but I am at my potentially most vulnerable and f–ked up in the romantic slice of the pie,” Paltrow said. “So it’s taken me a lot of work to get to the place where I have a good romantic relationship.

When the host mentioned Brad’s name, specifically, the Goop founder jumped in to say, “I f—ked that up, Brad.”

23. Aaron Carter

Aaron Carter and Hilary Duff met on the set of Lizzie McGuire in 2001, and dated for almost two years before he decided to start also dating Lindsay Lohan.

Of course, he forgot to tell Hilary.

As Carter explained, “I started dating Hilary [Duff] on my 13th birthday. I was dating her for like a year and a half and then I just got a little bored so I went and I started getting to know Lindsay [Lohan], dating Lindsay.”

A love triangle began and caused a tense feud between the women.

While the Lizzie McGuire alum is happily married with children, her former boyfriend is still convinced he has a chance.

“Don’t be that stupid d–– that loses the love of your life forever. Like me ” he Tweeted after her first marriage ended. “I’ll spend the rest of my life trying to better myself to get back to her. I don’t care what ANY of you think.”

When a fan asked if he was referring to Duff, he answered simply, “sure am.”

24. Khloé Kardashian

After the Tristan Thompson and Jordyn Woods cheating scandal rocked her world and broke her family, Koko regrets how she handled the breakup.

As documented on Keeping Up With The Kardashians, she ended the relationship and cut off all ties to Woods.

In a “drunken rage” in Palm Springs, she calls a friend of Thompson’s and screams into the phone that her ex-boyfriend is a “f—cking liar.”

On Twitter she wrote watching herself during that time makes her “so uncomfortable and cringe.”

She has since revealed that she has forgiven Tristan and Jordyn and is not holding a grudge against either of them.

“I know everybody makes mistakes. I think it’s how you handle it, and I think apologies need to be as loud as your disrespect, or to me it’s not sincere,” she said On Air With Ryan Seacrest. “I’m forgiving. I’m forgiven. I’m not someone who holds a grudge. If I do that it’s only going to affect me. That chapter is closed for me.  I want all of us to move on and to be happy, successful people. I just want everyone to just be better people with each day. That’s genuinely how I feel.”

25. Jude Law

Jude Law is still sorry for his infamous affair with the nanny of his children with Sienna Miller.

The cheating scandal turned him from beloved to liar overnight, prompting him to publicly apologize for his actions.

He said he was “deeply ashamed and upset” over what he did to his fiancé and family.

“Following the reports in today’s papers, I just want to say I am deeply ashamed and upset that I’ve hurt Sienna and the people most close to us,” Law said in a statement released Monday to the British Press Association.

He added: “There is no defense for my actions which I sincerely regret and I ask that you respect our privacy at this very difficult time.”

26. Brad Pitt

Brad Pitt and Jennifer Aniston’s divorce devastated Hollywood. To make things worse, their ending and his affair with Angelina Jolie during their marriage became fixation for tabloid drama.

A source told Us Weekly that Pitt “of course wishes he’d handled the end of their marriage in a more thoughtful manner.” The actor even “asked for Jen’s forgiveness a long time ago and she gave it,” the insider added.

According to In Touch, sources say he’s “come to realize that leaving Jen for Angelina was one of the biggest mistakes of his life.”

27. Kristen Stewart

Cheating on her Twilight co-star Robert Pattinson still haunts the actress.

She calls her infidelity one of her biggest regrets ever.

“I’m deeply sorry for the hurt and embarrassment I’ve caused those close to me and everyone this has affected,” she said in a public apology. “This momentary indiscretion has jeopardized the most important thing in my life, the person I love and respect the most, Rob. I love him, I love him, I’m so sorry.”

Her fling was with her Snow White and the Huntsman director, Rupert Sanders.

28. Kourtney Kardashian Regretted Leaving Scott Disick

Kourt, who shares three kids with Scott Disick over their nine-year relationship, reportedly wished she hadn’t left Scott.

It was reported she had broken up with her longtime love, so he would seek help for his addictions and emotional issues.

In 2015, a source told US Weekly, “”Kourtney’s shocked Scott isn’t begging her to take him back.”

29. Selena Gomez

The singer regrets a lot of things since her multiple splits from Justin Bieber.

After he posted pictures with his former girlfriend with Sofia Richie, fans were extremely critical, and Selena jumped in with some additional shade.

Selena wrote, “If you can’t handle the hate then stop posting pictures of your girlfriend lol – it should be special between you two only. Don’t be mad at your fans. They love you.”

All the messages caused him to briefly disable his account, then go on private.

Selena ultimately wrote on Snapchat, “What I said was selfish and pointless.”

30. Princess Diana

Princess Diana regretted her wedding to Prince Charles and described her big day as the “worst day of my life,” Reader’s Digest reported.

Despite trying to get out of the marriage, her sisters told her it was too late.

In National Geographic’s documentary, “Diana: In Her Own Words,” Princess Diana confessed her sisters said, “Your face is on the tea towel, so you’re too late to chicken out.”

Her husband, Charles, felt the same way.

“I desperately wanted to get out of the wedding in 1981, when during the engagement I discovered just how awful the prospects were, having had no chance whatsoever to get to know Diana beforehand,” the Prince of Wales reportedly confided to a friend.