Alanis Morissette and Ryan Reynolds
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Alanis and Ryan met at Drew Barrymore's birthday party in 2002. In June 2004, the "very passionate" duo became engaged. After a nearly three-year engagement, Reynolds and Morissette announced their separation.
Jennifer Aniston and John Mayer
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The guitarist and Friends alum dated on and off from 2008 to 2009. He admitted to Playboy that he slept with "four or five" women during his break from Aniston.
Selena Gomez and Justin Bieber
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Justin Bieber and Selena Gomez had an intermittent romance that lasted from 2010 to 2018. The two first met in 2009, when their managers introduced them after Bieber revealed in an interview that Gomez was his type.
Katy Perry and Russel Brand
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Katy Perry first met her ex-husband Russell Brand while filming a romantic scene in his 2010 film Get Him to the Greek. The American Idol judge said in June 2013 that Brand had ended their relationship via text message.
Kim Kardashian and Pete Davidson
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Kim and Pete started dating in October 2021 and he even got several tattoos of her (the one that said "my girlfriend is a lawyer" was our favorite!), before breaking up about nine months later.
Nicole Kidman and Lenny Kravitz
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Nicole Kidman was briefly engaged to rocker Lenny Kravitz. At the time, their relationship was kept secret. Kidman broke the story in an interview in 2017.
Taylor Swift and Harry Styles
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In 2012, Taylor Swift and Harry Styles briefly formed one of pop's most iconic couples. They broke up in 2013.
Miley Cyrus and Liam Hemsworth
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Miley Cyrus and Liam Hemsworth first met and fell in love as teenagers, during the filming of The Last Song in 2009. In the years that followed, they embarked on a passionate love affair that lasted into their twenties and resulted in two engagements, a marriage and, eventually, a divorce.
Courteney Cox and Michael Keaton
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In 1989, Courteney met Michael after telling a mutual friend how much she'd enjoyed his performance in the film Clean and Sober. The couple stayed together for six years before separating in 1995.
Ryan Gosling and Sandra Bullock
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Ryan Gosling and Sandra Bullock met on the set of Murder by Numbers and dated for about a year. Ryan later told Us magazine that Hollywood was responsible for their breakup, calling show business "evil".
Macaulay Culkin and Mila Kunis
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Mila and Macaulay were together between 2002 and 2011, and met when she was 18 and he 21.
Nick Cannon and Kim Kardashian
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Before Kim became famous, she dated Nick between 2006 and 2007, but when her infamous sex tape was leaked, her relationship with Nick ended. In a 2012 interview with Howard Stern, Nick revealed that they broke up because Kim lied to him about the tape's existence.
Sarah Jessica Parker and Robert Downey Jr.
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After meeting on the set of the 1984 film Firstborn, Sarah and Robert began a relationship that lasted eight years, but slowly fell apart due to Robert's drug addiction.