17 Celebrities Regret Breakups With Other Celebs

Celebrities are just like us. They fall in love, get into fights, get married, and break up – just like we do. And also just like us, they sometimes massively regret their breakups. Unlike us, they get to tell the world (and, indirectly, that person) all about their regrets. Some of the biggest relationships in Hollywood have ended in Splitsville. And while the all-too-typical joint statements always say it was mutual, and they’ll remain friends, we totally know that’s BS. Especially when one party starts touting their regret over the breakup!

Lucky for us, we get to hear celebs spill all the tea about their relationship regrets. Whether it’s in interviews or Instagram comments, some things don’t stay secret for long. And as much as it sucks to go through a break up in general, it has to suck more when your ex is just as famous as you are and you have to read tabloids about their next conquests! Watching your ex succeed while you still pine for them is the worst. Here are some celebrities that have expressed regret for breakups with their celeb partners!

17. Rita Ora, about Calvin Harris

These two had a very public relationship and an equally public breakup. Post-breakup, though, Ora seemed to have regret losing who she called “the right guy” just at the “wrong time.” Their jet-setting lifestyle drew them apart as they were both growing their careers and frequently apart. Trying to be in a long distance relationship while also being Hollywood megastars can’t be easy! It seems that if the two had been able to see each other more, this breakup would never have happened!

16. Common, about Serena Williams

It was exciting to see these two celebrities from different worlds come together. Unfortunately, the singer/actor and tennis star just couldn’t make it work. While Serena blamed their conflicting schedules (calling out him for being even busier than her!), Common has never been anything but complimentary about his ex in the press, even going so far as to posit at one point that if they got together again while in different places in their lives they would probably make it work. Seems like someone wasn’t ready to let their relationship die! He also straight-up told the media after their breakup that he still had a love for her. It doesn’t get more obvious than that!

15. Olly Murs, about Francesca Thomas

Pop singer Murs enjoyed a three-year relationship with his property management honey before they called it quits. Years after the split, he admitted his intense regret in an interview. In an interview, he said,

“I think I broke my own heart by letting my ex-girlfriend go. But that’s my own fault. That’s probably the last time my heart was broken. It was one of those ones where you break up with someone and you don’t really realize for about a year after that, actually, you’ve made a big mistake.”

Dang! And this was years after the split that he was professing his regret. Sounds like she’s the one who got away! Murs even wrote about their relationship, and the end of it, on his 2016 album 24 Hrs. While the two never got back together — Thomas is currently engaged to someone else — here’s to hoping he finds a love like that again!

14. Jef Holm, about Emily Maynard

Breakups from The Bachelorette world are pretty commonplace. But regret over those short-lived romances isn’t as common. Cue Jer Holm, the winner of Emily Maynard’s heart and her eventual fiancé. The two seemed super happy after the show ended, but eventually, they ended their relationship. The same spiel of “we’ll always be friends” and “no ill-will” was spilled by their statements, but Holm’s had something else to say later on. In a tweet, he said, “if u have a good girl hold on to her tight! They are hard to come by these days…” Eek sounds like someone was lamenting lost love! While the two stayed split and Maynard eventually married someone else, we can’t help but wonder if the two would have worked out if they had given it another shot!

13. Michael Douglas, about Catherine Zeta-Jones

This Hollywood power couple has been together since the late ’90s, but when they split in 2013, it seemed like another celebrity relationship bit the dust. But then they got back together! Douglas expressed his regret that their split ever happened in the press. They both got caught up in their lives outside of each other and drifted apart. He also expressed regret that he didn’t appreciate what he had right in front of him sooner! Even beyond his words, his actions spoke loudly about his regret for the split, considering the two worked hard to reconcile and have been going strong ever since. Sometimes celebrities can make it work!

12. K-Ci, about Mary J. Blige

These two hip-hop superstars were in a relationship for 12 years before they split. Their tumultuous and at times abusive relationship wasn’t always easy, though, and their issues led to their inevitably rough breakup. Years after, K-Ci expressed his regret for the way he acted in the relationship, which led to them falling apart. He notes that Blige did nothing wrong when they were together and he had done some shady things. Hindsights 20/20, though, and if you’re not going to treat a girl right, get ready to lose her!

11. Eric Benet, about Halle Berry

If you’re married to Halle Berry, you’re a pretty lucky guy. Too bad Eric Benet screwed it all up for himself. The singer cheated on the famed actress which led to their eventual breakup. He entered rehab for sex addiction shortly after. Obviously, despite his screw-ups, losing Berry was a major regret of his. He went on to say that he loved her very much but couldn’t give his all to the relationship, something he wishes had been different. Benet also said that he doesn’t blame Berry for dumping him! Though, let’s be honest, no matter what, you never regret getting dumped by Halle-freaking-Berry.

10. Burt Reynolds, about Sally Field

Reynolds and Field were the sort of celebrity power couple that doesn’t come along often. Then two dated for five years in the late ’70s and to this day he calls her the love of his life! In an interview, Reynolds said,

“Sally Field. I did four movies with Sally and spent five years with her. She was the love of my life and I screwed the relationship up. That sense of loss never goes away. I have no idea what Sally thinks about it. She could pick up the phone and speak to me but she never does. I spoke to her son recently. He said that his mum talks about me all the time. Maybe she’ll phone me one day. I’d love to have that conversation.”

Now we’re totally wondering what that conversation would be like! Neither of the stars is married, just sayin’!

9. Lamar Odom, about Khloe Kardashian

Celebrities can be pretty silly when it comes to matters of the heart. Like marrying someone they barely know! Kardashian and Odom got married after three weeks of dating in 2009, and it’s all kind of been downhill since. Their married was rife with Lamar cheating, using drugs, and his rapidly declining basketball career. Eventually, they split, though Khloe was always there for him even when he had multiple strokes and heart attacks after collapsing in a brothel. The two eventually officially divorced, but now that he’s sober, he has a lot of regrets about how everything went down. His biggest regret? Cheating on his former love, like, so many times. He publicly never wanted to divorce his former wife, but luckily, he seems much healthier now with or without Kardashian!

8. Courteney Cox, about David Arquette

For a long time, Courteney Cox was known better as “Courteney Cox-Arquette.” Suddenly, that all changed when the two split in 2010 and were later divorced in 2013. Speaking about the divorce, she says the two tried, but of course, there are regrets — noting that “in divorce you always have regrets.” She especially didn’t want to go through the divorce for the sake of her and David’s child together, regretting bringing that into her childhood. The two celebrities seem to be on incredibly amicable terms, though, and are separately with other people now.

7. John Stamos, about Lori Loughlin

Turns out Uncle Jesse and Aunt Becky were almost a real-life thing! Except, according to Stamos, she’s totally the one that got away. The two once went on a date when they were much younger, but it seemed that the timing was always off for these would-be lovebirds. When was one single, the other was taken, and vice-versa for many years. Stamos has expressed regret that they never really went for it though, and left it at that single date. Not gonna lie, we totally would have been on board with this relationship!

6. Kris Jenner, about Robert Kardashian

These two are the reason we have Kardashians running around everywhere now. So… thanks? Sadly, after they had their “Kute” kids, they ended up divorcing and as we all know Kris got remarried to Caitlyn Jenner, who came out as trans shortly after they divorced, but that’s not the breakup Kris regrets — she regrets ever leaving Rob Sr.! In an interview, she straight-up said, “The one regret, if I had to do it over, would be divorcing Robert Kardashian.” Doesn’t get more blatant than that! There’s only one thing though. If they hadn’t gotten divorced, the world wouldn’t have gotten Kylie Jenner and Kendall Jenner. Y’all can decide if that would’ve been a good thing or not.

5. Sean Combs, about Cameron Diaz

If you’re anything like us, you totally forgot these two ever dated, let alone broke up! Sometimes celebrities pair up in the strangest of ways. Anyways, these two were a hot item for a few years in the early ’00s. The two were off-and-on for a while, eventually going their separate ways for various reasons. But it seems the rapper never really got over the woman he called, “the sexiest girl in the world!” Reportedly, around the time Diaz began dating her now-husband Benji Madden, Combs said that if he could turn back the clock, he would do things differently when it came to her. Too little, too late P. Diddy!

4. Robin Thicke, about Paula Patton

Sometimes you think a celebrity couple is destined to make it. These two had been together since their teen years and spent 21 years as a couple before Patton filed for divorce in 2014. Thicke had enjoyed some mild success as a musician until 2013’s “Blurred Lines” made him a household name and changed everything. Changes in Thicke’s lifestyle and cheating allegations seemingly led to them announcing their split early the next year. After they separated, though, he seemed to be doing the most to get her back. He dedicated songs to her at concerts and let fans know he was trying to win a reconciliation. He even dropped an album months later titled Paula, dedicated to their relationship and split. Unfortunately, it didn’t work, and their divorce was finalized soon after.

3. John Cena and Nikki Bella

There was regret on both sides of this shocking – and short-lived – breakup! The two wrestling stars announced their split early in 2018, a few weeks ahead of their wedding. Bella called off the engagement to her beau of six-years reportedly because she could tell he had cold feet and his reluctance to have children ultimately became a deal breaker. Despite being the one who broke up with him, she was publicly upset about the entire thing and said she missed him. Cena also publicly said that it was hard and he missed her and even went so far as to announce live on TV that he was suddenly ready to have children with Bella if she’d take him back. By the next week, the two were basically back together after we all wondered why two people who clearly didn’t want to break up ever did!

2. Aaron Carter, about Hillary Duff

Even celebrities aren’t immune to never getting over that one person. These two dated when they were teen stars in the early ’00s (Y’all remember the love triangle between them and Lindsay Lohan, right?). They eventually broke up as every teen couple does and went on and led separate lives. Then Carter dropped the BOMB in 2014 when he went on a tweeting spree about still having love for Duff. In the tweets, he says he was a “stupid douche” who “lost the love of [his] life forever.” He also added that “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.” Yikes, dude. In response to the tweets, Duff said in an interview that they don’t really know each other so it’s a little weird. Celebrities don’t just have relationship regrets, they have their crazy relationship moments, too!

1. Taylor Swift, about Taylor Lautner

Swift is the queen of lamenting her past relationships via song, and her time with Lautner was no different. Her song “Back to December” is widely believed to be about her breakup with Lautner — and how much she regrets it! Lautner pretty much confirmed it was about him on a press tour and had us re-analyzing the lyrics all over again. In the song Swift says,

“It turns out freedom ain’t nothing but missing you / Wishing I’d realized what I had when you were mine.”

Those are some breakup regrets if we’ve ever heard them! While most of Swift’s songs about her ex’s hurting her, or about the good times in a relationship, this is one of her only songs about regretting hurting someone else. And we can see why she’d regret it — have you seen Taylor Lautner?!

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