Trending Now: 13 Celebrities’ Most Heartbreaking Relationship Regrets – Fans React

A relationship ending doesn’t change the fact that love was there. Sometimes, two people simply aren’t meant to be together — but that doesn’t mean it doesn’t hurt to be apart.

Here are 13 celebrities’ most heartbreaking relationship regrets:

1. THE RELATIONSHIP: Ben Affleck and Jennifer Garner were married from 2005 to 2018. They met on the set of Pearl Harbor in 2000 and became a couple four years later. However, they announced their plans to divorce shortly after their 10th anniversary. In 2016, she shut down rumors he’d had an affair with their nanny, telling Vanity Fair, “It was a real marriage. It wasn’t for the cameras. And it was a huge priority for me to stay in it. And that did not work. … We had been separated for months before I ever heard about the nanny. She had nothing to do with our decision to divorce. She was not a part of the equation. Bad judgment? Yes. It’s not great for your kids for [a nanny] to disappear from their lives.”

THE REGRET: In 2020, Ben told the New York Times, “I drank relatively normally for a long time. What happened was that I started drinking more and more when my marriage was falling apart. This was 2015, 2016. My drinking, of course, created more marital problems. … The biggest regret of my life is this divorce. Shame is really toxic. There is no positive byproduct of shame. It’s just stewing in a toxic, hideous feeling of low self-worth and self-loathing. It’s not particularly healthy for me to obsess over the failures — the relapses — and beat myself up. I have certainly made mistakes. I have certainly done things that I regret. But you’ve got to pick yourself up, learn from it, learn some more, try to move forward.”

2. THE RELATIONSHIP: Al Pacino and the late Diane Keaton were in an on-and-off relationship for about a decade and a half. After meeting on the set of The Godfather in 1972, they started dating two years later. However, they broke up for good in 1990 because she was ready to get married and gave him an ultimatum. She later told People, “I worked hard on that one. I went about it in not a perfect way.”

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THE REGRET: According to Vanity Fair, he reportedly called her the “love of his life” and regretted not marrying her.

3. THE RELATIONSHIP: Justin Bieber and Selena Gomez were in an on-and-off relationship for nearly a decade. After their first date in December 2010, they were together for about two years. They got back together around the end of 2015, but it didn’t last long. Then, in the fall of 2017, they seemingly rekindled their relationship, but they broke up for good the following March. Six months later, he married Hailey Bieber.

THE REGRET: In November 2015, Justin told i-D that they got into a serious relationship too young. He said, “I think with that relationship… I put so much of myself on the line with her, because I was so distant with everyone else. So it’s like, you have the world who’s loving you, but it’s not like they know my heart — they don’t know me. So when I found that love, I was just like, ‘Woah, I want to hold on to this.’ And I just put everything into it, and in reality, there’s just no holding back. You’re just like, ‘This love feels so good.'”

THE RESPONSE: In January 2016, Selena addressed a recent video of Justin singing to her before an awards show. She told Rolling Stone, “Well, I am sorry, first of all. And honestly, what I would love to be printed is that I am so beyond done with talking about that, and him. … I don’t alter my life because of what people are going to talk about. If I go and have a great time, I live my life, and nothing is going to dictate how I feel unless I let it.”

4. THE RELATIONSHIP: Amber Rose and Wiz Khalifa started dating in 2011 after he publicly expressed his interest in her in an interview. They fell hard and fast, getting engaged and welcoming their son, Sebastian, the following year. They got married in 2013, separated in 2014, and finalized their divorce in 2016.

THE REGRET: In 2023, Amber told the No Jumper podcast, “With Wiz, I cried for, like, three years straight. … Wiz was the love of my life. I used to just sit in the shower and be like, ‘****.’ He feels the same way. We’ve had this conversation. He’s said it in interviews and stuff like that. We were each other’s soulmates, and I think that’s why we’re able to still be close and coparent.”

5. THE RELATIONSHIP: Kris Jenner and the late Robert Kardashian Sr. got married in 1978 and had four children together. However, they divorced in 1991, two years after Kris had an affair. In her 2011 memoir Kris Jenner… and All Things Kardashian, she wrote, “I had lost Robert. Suddenly, I realized everything that was great about my marriage. Robert was the greatest guy in the world. He would never cheat on me. He only wanted the best for me.”

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THE REGRET: On a 2023 episode of The Kardashians, Kris told her daughter Khloé, “I think being really young and dumb is something that plays into it, because you don’t really understand the consequences of your actions. … He was such a great husband and such a great dad, and I think that I fell into a situation where I thought that the grass was greener somewhere else, and I made a huge mistake. That’s, like, my life’s biggest regret.”

6. THE RELATIONSHIP: Shortly after Elizabeth Taylor’s third husband, Mike Todd, died only a year into their marriage, she began an affair with Eddie Fisher, who was married to her longtime friend, Debbie Reynolds. Eddie left Debbie and married Elizabeth in 1959. However, they divorced in 1964 after her affair with her Cleopatra costar Richard Burton.

THE REGRET: In the 2024 documentary Elizabeth Taylor: The Lost Tapes, she said, “I was keeping Mike alive by talking about him because Eddie, he was a great friend of Mike’s. That was the only thing we had in common, was Mike. I never loved Eddie. I liked him. I felt sorry for him. And I liked talking [to him]. But he was not Mike.”

7. THE RELATIONSHIP: Will Smith was married to Sheree Zampino from 1992 to 1995. They share one son, Trey.

THE REGRET: In 2020, Will addressed his first marriage on Red Table Talk, the talk show hosted by his current wife, Jada Pinkett Smith. He said, “With Sheree and with Trey, that was a really difficult time. Divorce was the worst thing in my adult life; divorce was the ultimate failure for me. I’ve been hurt a lot in my adult life, but I don’t think anything touches the failure of getting divorced from my 2-year-old son’s mother.”

THE RESPONSE: When Sheree appeared on Red Table Talk two years later, she said, “[‘Fail’ is] a heavy word because, if you remember, Will had said that this was his greatest failure. I had an issue with that because I didn’t understand how we could do what we do as a blended family, and do it as well as we do, and as loving as we do, and have an amazing son, and it’s looked at as a failure. It did what it was supposed to do, so that was successful. And that had to end so that something else could begin.”

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8. THE RELATIONSHIP: Tyrese Gibson and Samantha Lee got married in 2017 and welcomed their daughter in 2018. However, they announced their separation in 2020 and finalized their divorce in 2025. In a joint Instagram statement regarding their split, they said, “We have decided to make a statement of a painful and significant development in our lives. After much thought, consideration, and prayer, We unfortunately have made the difficult decision to officially separate & divorce. Our intention is to remain the best of friends & strong coparents. We feel incredibly blessed to have found each other and deeply grateful for the 4 years we have been married to each other.”

THE REGRET: In 2023, Samantha told the Hardly Initiated podcast, “It’s very important to seek wise counsel. You have to really decide and make a very calculated decision based on your belief systems. I think we do take divorce very casually. I would never tell a woman to walk through that in the same frame as I was when I did it. I was very, very hurt. I was very angry. I remember when I made the decision, I was hysterically crying on the phone with my attorney. I was not in any position to make that decision. I was extremely emotionally intoxicated.”

THE RESPONSE: On Instagram, Tyrese said, “Congratulations, you went viral again over something else you said because you are trying to build up your YouTube page to get your followers up. You packed up a 1-year-old, put a COVID mask on top of the Ring cameras and I was literally in an airplane on my way home to fight for my marriage and my family. You’re heartless. This is all about money.”

9. THE RELATIONSHIP: Nikki Bella and John Cena started dating in 2012 and got engaged in 2017 when he famously proposed in the wrestling ring. However, they reportedly called it off the following year because, after trying to shove down her dreams of having children to support his choice to be child-free, she realized she didn’t want a future without kids of her own.

THE REGRET: In 2021, Nikki told Health magazine, “The one thing I really regret about showcasing the breakup [on her reality show Total Bellas] is that no one got to hear [John’s] voice, and it just seemed so one-sided. I felt like that wasn’t fair to him because he was on this journey with us from the beginning. … He was fully there to support me. I’ll never forget his support and his love. That’s what made me sad. I don’t want to say it became the Nikki show, but in a way it did because you didn’t get to see John anymore.”

10. THE RELATIONSHIP: Taylor Swift and Calvin Harris dated for 15 months between 2015 and 2016. After they broke up, he tweeted (and later deleted), “The only truth here is that a relationship came to an end & what remains is a huge amount of love and respect.” She retweeted his message.

A few weeks later, Taylor began publicly dating Tom Hiddleston. Calvin seemingly crashed out in a series of since-deleted Instagram comments, purportedly writing, “[Taylor] controlled the media and this situation, I had no idea what was going on. So that kind of makes it a lot worse from my perspective” and “[I am] not jealous sir, FREE.” However, speaking to E! News, a source denied that he wrote the comments. In the wake of her new romance, Taylor and Calvin unfollowed each other and deleted any trace of their past relationship from their social media profiles.

Then, about a month after their breakup, the fallout reached a fever pitch when Taylor’s reps confirmed to People that she wrote “This Is What You Came For,” Calvin’s hit song with Rihanna, under a pseudonym. In response, Calvin went full scorched earth on Twitter.

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THE REGRET: A year later, Calvin told British GQ, “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. It’s very difficult when something I consider so personal plays out very publicly. The aftermath of the relationship was way more heavily publicized than the relationship itself. When we were together, we were very careful for it not to be a media circus. She respected my feelings in that sense. I’m not good at being a celebrity. But when it ended, all hell broke loose. 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.”

11. THE RELATIONSHIP: Jennie Garth and Peter Facinelli met while filming An Unfinished Affair in 1995 and got engaged four years later. They were married from 2001 to 2013 and share three children.

THE REGRET: On a 2024 episode of her podcast I Choose Me, Jennie said, “When you first start a relationship with somebody, you don’t think about, what are we gonna do if this doesn’t work out? Like, how am I gonna coparent with this person? So, we settled on shared custody, 50/50. I know for me, there were times when I really emotionally regretted that decision and not fighting harder for more.”

THE RESPONSE: Peter, who was a guest on that episode, replied, “I mean, it was always hard. I think, listen, coparenting is hard. Divorce is hard. I didn’t have a model for it. My parents weren’t divorced. … Our kids are on the other side of it. Our kids turned out really wonderful, and I feel like they needed both of us. You know? They really did benefit from having both of us.”

12. THE RELATIONSHIP: LisaRaye McCoy got engaged to Turks and Caicos Islander Premier Michael Misick three months after they met. They were married from 2006 to 2008.

THE REGRET: Appearing on Out Loud with Claudia Jordan in 2020, LisaRaye said, “For me, hands down, I should have married for love. … It was the potential of falling in love, but I should have been in that before the marriage. The dream he sold me was, ‘I want to date you in our marriage.’ I had never heard of that before, and I was thinking, that’s kind of clever! And we’re going towards that way anyway, so okay. We can accomplish what we’re trying to accomplish sooner in a partnership. In a partnership. A partnership is what I thought I was getting into.”

13. And finally, THE RELATIONSHIP: Mila Kunis and Macaulay Culkin dated from 2002 to 2011. A year after the breakup, she told Elle, “Being settled so young really helped. You know, I wouldn’t take back anything in my life, not one thing. I think it all shaped me to be who I am today. There are things that people know about, and there are things that the press doesn’t know about, and everything that did occur 100 percent shaped who I am. My ex-boyfriend, my family, my friends, everybody.”

THE REGRET: However, in 2018, Mila told the podcast Armchair Expert, “I was an *** in my 20s, and I’ll be the first to admit it. And that’s something that took me a long time to come out and be like, ‘Yeah, you know what, I was a ****,’ and accept it, and I own it now. It’s ****** up what I did, and it’s ****** up how I did it. When I got to be single, I said, ‘I just need to figure myself out.’ I genuinely need to know why I did what I did, and, like, regroup myself as a human being.”

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