17+ Big Dating Regrets Celebs Had To Live With

mason.zimmer 21 Nov 2018

As Jay-Z once rapped, "In order to survive, gotta learn to live with regrets." More recently, he got a lot more specific about what those regrets are, but we'll get to that in a moment.

The point is that no matter who we are, we can point to at least a couple of things in our lives that we would've done differently if we had the chance. And with all the mistakes and hurt feelings that can come from a relationship gone wrong, it's no surprise that a lot of our regrets come from the dating world.

As you're about to see, this doesn't get any less true for those in the public eye.

Noah Cyrus expressed regret for dating Lil Xan.

Instagram | @noahcyrusteam

At least, that's what Us Magazine reported when they saw her make an Instagram comment saying "my last relationship was the mistake" on a meme about people's biggest mistakes in relationships.

Gee, what an unexpected revelation.

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Kris Jenner wishes her marriage with Robert Kardashian didn't end the way it did.

She said that an affair with a soccer player led the marriage to fall apart and considers that one of the biggest regrets in her life.

She also said she considered Robert's filing for divorce devastating because "it made it real."

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Jay-Z regrets cheating on Beayoncé no matter many great albums it inspired.

Instagram | @jayzmrcarter

The entertainment mogul told the New York Times that the hardest part was "seeing pain on someone's face that you caused, and then have to deal with yourself."

He said the couple made the Lemonade and 4:44 together and treated both albums like therapy, which seemed to help them navigate that difficult chapter in their lives.

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Pete Davidson is definitely not rocking any of his Ariana Grande tattoos anymore.

Instagram | @petedavidsonrares

Seventeen reported that Pete has since covered up his Dangerous Woman-inspired bunny mask tattoo with a black heart and covered the "H2GKMO" tattoo on his hand with a black arrow.

The second one apparently stands for "Honest to God, knock me out," which is one of Ariana's signature phrases.

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Kim Kardashian wishes she had started dating Kanye West sooner.

Instagram | @kanyewestt_official

Kim said they had done some friendly flirting before she married Kris Humphries, but their romance hadn't clicked until she had made what she called "So many mistakes that must have hurt Kanye."

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Kristen Stewart called her affair with director Rupert Sanders a "momentary indiscretion."

YouTube | Movieclips

Unfortunately, this indiscretion was would end up costing her a relationship with her Twilight co-star Robert Pattinson. Since her statement about the affair was also a declaration of love for Robert, it was clear that she regretted this indiscretion deeply.

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Nicole Kidman doesn't necessarily regret marrying Tom Cruise, but wishes she hadn't rushed into marriage so young.

Twitter | @sophwilkinson

She said she looks back in disbelief at how young she was and compared where her life was in her 20's to Taylor Swift's place in life.

As [she put it], "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."

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Looking back, Jada Pinkett-Smith said she shouldn't have dated Will while he was technically married.

Instagram | @willsmith

She said on her Facebook show, Red Table Talk, that she pursued the relationship because she didn't fully understand what it meant to be married and go through a divorce at the time. Knowing what she does now, she said she probably should've "fell back."

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Britney Spears now believes that she married Kevin Federline for the wrong reasons.

Instagram | @britneyspears

Us Magazine reported that she said in the documentary Britney: For The Record that she married him for the idea of married life rather than because she followed her heart into something that would truly make her happy.

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Without getting specific, Courteney Cox experienced some regrets after divorcing David Arquette.

Twitter | @CourteneyCox

The two remain friends and she said she wanted him to be happy even if it wasn't with her, but there are some things she would've liked to do differently.

As she put it, "In divorce you always have regret. We were married for a long time, so it's not like we didn't try."

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Robin Thicke now realizes he shouldn't have been so quick to make an album about his issues with Paula Patton.

Instagram | @robinthicke

The "Blurred Lines" singer told Hot 97 that he wished he had taken the time to sort out his personal life before jumping into his usual method of making autobiographical music.

This was because releasing the Paula album so quickly gave people the impression that he was trying to sell his personal drama.

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Burt Reynolds considered Sally Field the love of his life and wished he never pushed her away.

YouTube | Movieclips

Even though their relationship ended back in the 80's, Burt Reynolds told Vanity Fair in 2015 that he still missed her terribly and that thinking of her was still hard on him over 30 years later.

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Calvin Harris regrets taking his post-breakup issues with Taylor Swift to Twitter.

YouTube | Clevver News

Billboard reported that Calvin said this was, "The wrong instinct."

It didn't help their breakup was around the time Taylor revealed that she co-wrote "This Is What You Came For," so Calvin's angry tweets about Taylor "tearing" him down happened partially because he thought his talent was being belittled.

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Cher wishes she wasn't too nervous to go out with Elvis Presley.

Twitter | @LevysDigest

As she said on The Late Show to David Letterman, she had the chance to go out with Elvis, but was so nervous that she never actually made it to the date. She also said she regrets not going further with Marlon Brando than just hanging out a few times.

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Aaron Carter wishes that he never pushed Hillary Duff away.

Twitter | @aaroncarter

At least, that's what Billboard reported that he expressed in a series of tweets where he said he wanted to win her back and regretted breaking up with her.

This happened after Hillary separated from her husband, but she apparently wasn't interested in rekindling anything with Aaron.

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Nick Lachey said that making a reality show with Jessica Simpson was a dumb idea.

YouTube | xx1jessicafanxx

While he said that Newlyweds: Nick & Jessica was enjoyable at first, it became invasive and put a strain on his marriage with Jessica. He knew it wasn't entirely fair to blame their divorce on the show, but named it as a factor nonetheless.

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Michael Douglas blames his separation with Catherine Zeta-Jones on the fact that he took their marriage for granted.

Instagram | @catherinezetajones

After the two rekindled their relationship in 2014, Michael told The Sun that he wasted a lot of energy making a good impression on strangers when he should have been focusing that energy on his family.

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Gwyneth Paltrow has admitted to messing up a lot of her relationships.

Instagram | @gwynethpaltrow

At least, that's what USA Today reported that she said on the Girl Boss podcast.

She specifically admitted to messing up her relationship with Brad Pitt, but said that she's generally at her most vulnerable "in the romantic slice of the pie."

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Melissa Joan-Hart regrets not taking the chance to link up with Ryan Reynolds.

YouTube | daphschizo

The two acted together in the Sabrina The Teenage Witch movie and she told Studio 10 that they were both smitten, but she didn't go through with it because she had a boyfriend at the time.

In hindsight, however, she said that she wished she had taken the chance because her relationship at the time didn't work out anyway.

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Sienna Miller wishes she had been a more established actor before she ended up with Jude Law.

Instagram | @siennamiller1

She said that she hates the idea of regretting their relationship despite his infidelity.

Still, she said that part of her wishes she had a movie before their relationship got so much press attention because it made her have to fight to be regarded for her work.

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John Stamos considers Lori Loughlin the one that got away.

YouTube | COAFkids

He told HuffPost Live that he briefly dated his Full House co-star, but the timing was difficult because she was married for a lot of the time they shared the screen together.

Although he considers her a dear friend and said that's good enough, that feeling that he missed the boat still lingers.

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Rita Ora wishes she had met Calvin Harris at a different time in her life.

Instagram | @ritaora

She told Cosmopolitan that both of them were too busy to see each other while they were dating, which led her to consider him the right guy at the wrong time.

The long-distance relationship life is not the life for her.

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Ben Mackenzie generally regrets not listening more in relationships.

Instagram | @mrbenmckenzie

The O.C. star didn't mention anyone in particular when he said this, but he told Elle Magazine that his ego would get in the way and said that if he listened more, he would have likely recognized times where he was being too jealous and competitive much earlier.

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Nick Viall regrets revealing that he slept with Andi Dorfman while she was on the Bachelor.

Instagram | @nickviall

The reality TV star told People that the subject wasn't taboo to him, but he hadn't realized what problems it would cause for Andi.

As he put it, "I regret that in the sense that it unnecessarily and unfairly caused Andi to get a lot of flack."

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