15 Celebrity Breakups That Broke Our Hearts

There are just some celebrity couples we can't help but root for. Maybe they just have off-the-charts chemistry on the big screen in a movie we love. Maybe they were the pop idols we obsessed about when we were teenagers. Or maybe they were both so sexy we couldn't help but gawk. Whatever the reason, there were some celebrity couples we were totally fascinated by. They seemed like they might be the ones to defy the Hollywood odds and actually go the distance. And then, sadly, the love affair was over.

We've been thinking about some of the most shocking celebrity breakups of the couples we were rooting for, and we're not afraid to admit that these splits broke our hearts! Now we get it: Nobody really knows what might be happening in private in any relationship besides the couple in it, no matter how much they might share on Instagram or their own reality show.

We're not saying that these couples should have stayed together. Nor do we necessarily think they should get back together (many of these stars are remarried or otherwise happily involved). But we can't deny that we had a moment of feeling really bummed when we found out that these 15 famous couples had called it quits.

Lisa Bonet & Jason Momoa

Jason Momoa and Lisa Bonet seemed like they were ideally suited for each other, especially given that Lisa had been Jason's childhood crush. The couple was together for more than 17 years but called it quits in 2022 after five years of marriage. While it was a surprise to learn that they'd separated, we have to be honest: We're really curious to see if/when Lisa finds love again. After divorcing Lenny Kravitz and Jason Momoa, what handsome and cool person could be next for her?

Ali Wong & Justin Hakuta

While comedian Ali Wong's now ex-husband Justin Hakuta wasn't a celebrity in his own right, we felt like we kind of knew him through Ali's many jokes about the challenges and joys of marriage and parenthood in her standup specials. It had seemed like they were the perfect opposites-attract partnership, but the two announced their separation in 2022 after eight years of marriage.

Britney Spears & Justin Timberlake

Oh, man. Back in the day, Britney Spears and Justin Timberlake were the reigning king and queen of pop music, and it just made so much sense that they were a couple. Their 2002 breakup was a bit of a shock and, in hindsight, that period seemed to mark a turning point for Britney and the start of a long stretch of really turbulent years for her.

Jennifer Aniston & Brad Pitt

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It's not overstating it to say that people were outraged when Jennifer Aniston and Brad Pitt's marriage imploded in 2005, likely due to the existence of a bombshell by the name of Angelina Jolie. Almost overnight, people were rocking #TeamJen T-shirts, and the Friends star definitely won the sympathetic vote from the public.

Rhea Perlman & Danny DeVito

Danny DeVito and Rhea Perlman married in 1982 and just seemed so right for each other (and not just because they were a compatible height!). The pair separated in 2012, got back together, and then separated again in 2017. While they never officially divorced, their romantic relationship of 35-plus years seems over for good now.

Jessica Simpson & Nick Lachey

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Jessica Simpson and Nick Lachey were early stars of the reality TV genre, and viewers (including us!) got invited into their marriage for three seasons of Newlyweds. While it was clear from the show that the couple had some issues, it was also clear that they had real love at the start of their marriage, which ended up lasting only about four years. We can't help it — we were really rooting for them!

Sandra Bullock & Jesse James

Sandra Bullock and Jesse James were married from 2005 to 2010 and seemed, in the happier moments, like a classic opposites-attract relationship. When they announced their divorce, our hearts were broken — but not because we loved them together, but because he had the nerve to cheat on Sandra and break her heart. She deserved better!

Amy Poehler & Will Arnett

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It was easy for us to imagine that Will Arnett and Amy Poehler's nine-year marriage was filled with nothing but laughter because they are both so funny. But the truth is that marriage is hard for everyone, and we were a little heartbroken when Will revealed in an interview with Vanity Fair that the breakup was "almost excruciating — just brutal, brutal, brutal."

Gwen Stefani & Gavin Rossdale

It was 1995 when we found out that Gwen Stefani and Gavin Rossdale were together, basically making them one of the biggest couples in music and pop culture of the era. The two tied the knot in 2002 (her wedding dress is still iconic) and had three kids before divorcing after almost 13 years of marriage. It was a sad end to a story many of us believed was a rock 'n' roll fairy tale.

Jennifer Aniston & Justin Theroux

We think it is safe to say that we were all rooting for Jennifer Aniston to be lucky in love again after her marriage to Brad Pitt ended. And it seemed like she'd found that with actor Justin Theroux, whom she started dating in 2011 and married in 2015. Sadly, this one didn't last either, and we were bummed for Jen when she and Justin split in 2018.

Susan Sarandon & Tim Robbins

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Another couple who always just seemed effortlessly cool together and like they just made sense was Susan Sarandon and Tim Robbins. The duo was together for more than two decades — after meeting while filming the classic baseball move Bull Durham — before they split in 2009.

Julia Roberts & Lyle Lovett

OK, this might be a controversial choice, since a lot of people never thought the duo of mega-movie star Julia Roberts and goofy-seeming musician Lyle Lovett made a whole lot of sense. But that's kind of what we loved about it! They were a bit of an odd couple, but Lyle seemed to bring stability to Julia after her fairly dramatic dating life in her 20s.

Jennifer Garner & Ben Affleck

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Although Ben Affleck is now happily married to a different Jennifer (Ms. Lopez, of course) and Jennifer Garner seems to be flourishing in her post-divorce life, we still felt sad for the pair when they split. It had seemed like Jen especially fought really hard to make it work, and it's always sad when young kids are involved (they share daughters Violet and Seraphina and son Samuel).

Reese Witherspoon & Ryan Phillippe

One of the "it" couples of the late 1990s was Reese Witherspoon and Ryan Phillippe. We loved them in the cult classic film Cruel Intentions and were charmed when they quickly had two kids, daughter Ava and son Deacon, who are their carbon copies. The pair was married for seven years before sadly splitting in 2006.

Olivia Wilde & Harry Styles

When Olivia Wilde and Harry Styles started dating, she instantly became the subject of lots of gossip — and maybe a little jealousy! Really, who wouldn't be a tad envious of a mom in her late 30s getting to hook up with one of the hottest pop stars of the moment. Sadly for all of us living vicariously through Olivia, the two split up in December 2022.