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Princess Diana & Prince Charles
What happens at Kensington Palace doesn’t always stay at Kensington Palace. The Prince of Wales married the People’s Princess in 1981. Unfortunately, the two proved to be incompatible when it came out that they both had extramarital affairs. They separated in 1992 and their divorce was finalized in 1996. Roughly a year later, Diana died in a car crash while being chased by paparazzi.
Brad Pitt & Jennifer Aniston
The Friends actor married the movie star in 2000 after roughly two years of dating. But like many (er, most) celebrity marriages, it crashed and burned when Aniston found out that Pitt cheated on her with — you guessed it — Angelina Jolie.
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Ashton Kutcher & Demi Moore
Despite their 15-year age difference, Kutcher and Moore once were one of the most beloved couples in Hollywood — that is, until they announced plans to split in 2011. After first meeting in 2003, the pair wed in 2005. In her 2019 book, Inside Out: A Memoir, Moore gave some insight as to why they called it quits, explaining that Kutcher’s infidelity played a significant role.
Rachel McAdams & Ryan Gosling
Given their undeniable chemistry in 2004’s The Notebook and their subsequent smooch at the 2005 MTV Movie Awards, fans were equal parts shocked and heartbroken by Ryan Gosling and Rachel McAdams’ 2007 split. There was, however, a brief glimmer of hope when they seemingly rekindled their romance in 2008, but they broke up again shortly after.
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Madonna & Sean Penn
Madonna and Sean Penn were married in 1985 on her birthday and divorced four years later. The actor was allegedly physically violent and, at one point, he was accused of hitting the “Like A Prayer” singer with a bat. Around the time of their split, Madonna told Rolling Stone that it felt like the whole world was against them. More recently, she’s said some very nice things about him. “I want to say that, Sean, I love you,” she said at the 2016 gala. “From the moment that I laid eyes on you. And I still love you, just the same.”
Reese Witherspoon & Ryan Phillippe
Apparently, the couple that works together doesn’t always stay together. Witherspoon and Phillippe co-starred in the 1999 film Cruel Intentions. That same year, the couple exchanged their vows after two years of dating. They separated in 2006, with Phillippe citing their immaturity as the reason for their split.
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Katie Holmes & Tom Cruise
Affectionately referred to as “TomKat,” the couple got engaged in 2005 after making their debut that same year. In 2006, the pair wed in Italy and welcomed their daughter Suri later that year. In June 2012, the couple shocked the world when they announced their split — especially because there weren’t any major indicators that things had gone south in their relationship.
Ben Affleck & Jennifer Garner
The Hollywood couple, who the world came to know as “Bennifer,” first fell in love on the set of 2003’s Daredevil while both in relationships with other people. Garner was married to Scott Foley and Affleck was with J.Lo. But after calling off his engagement to the “Love Don’t Cost A Thing” singer, Affleck pursued Garner. The pair wed in June 2005 and had three children together. In 2015, they announced their split following allegations that Affleck cheated with the family’s nanny.
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Chris Pratt & Anna Faris
Hearts shattered everywhere when the news broke in 2017 that the Guardians of the Galaxy star and his then-wife were separating. The two actors share a son named Jack together and never gave an official reason for their split. In other words, many fans didn’t quite get the closure they needed. Regardless, the pair has moved on. Pratt is now married to Katherine Schwarzenegger and Faris is currently engaged to cinematographer Michael Barrett.
Jennifer Lopez & Alex Rodriguez
J.Lo & A-Rod seemed like the picture-perfect A-list couple throughout the entirety of their four-year-long relationship. The pair started dating in 2017, and the retired New York Yankees shortstop popped the question two years later. Due to the ongoing coronavirus pandemic, the couple had to postpone their wedding not once, but twice. As it turns out, it may have been a sign because, in April 2021, they made it clear that they would not be walking down the aisle at all.