38 Celebs You Totally Forgot Were Once Engaged

Celebrity relationships seem to be constantly in flux, which is why it can be pretty hard to keep up with who is dating who in Hollywood. And due to society's obsession over today's Hollywood power couples like Brad Pitt and Angelina Jolie, it can be easy to forget that there was a time when these couples didn't exist at all. In fact, these power couples could have looked pretty different if these stars wed — and stayed with — the other people they had intended to marry. Click through to read about celebrity power marriages that almost were.

Brad Pitt

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The World War Z actor is married to Angelina Jolie, but once upon a time he was set to wed this actress.

Gwyneth Paltrow

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The Se7en co-stars got engaged shortly after filming the 1995 film together, but split after two years together.

Kanye West

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The rapper is happily married to reality star Kim Kardashian, but before that he was engaged to this celebrity.

Amber Rose

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Rose claimed that West cheated on her with his now-wife, which led to the end of their longterm relationship.

Kiefer Sutherland

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The 24 star was set to marry America’s sweetheart before she bailed on their wedding.

Julia Roberts

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Roberts left her fiancé Sutherland in 1991, just three days before they were set to marry. The kicker? She allegedly ran off with his best friend, Jason Patric.

Courteney Cox

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The Friends star dated this actor for years but could never make the jump to marriage.

Michael Keaton

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The Birdman actor and Cox broke things off after years of dating in 1995, allegedly due to the fact that Keaton just couldn’t bring himself to commit.

Tara Reid

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This engagement was probably the most early ’00s thing to happen ever.

Carson Daly

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The NBC host and the Josie and the Pussycats actress were set to be married until Reid allegedly got cold feet and called off the wedding.

Winona Ryder

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The ’90s icon was engaged to her Edward Scissorhands co-star but they never made it down the aisle.

Johnny Depp

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Depp was so in love with then-fiancee Ryder that he got “Winona Forever” tattooed on his arm. When the pair split before the wedding, Depp had the tat changed to say “Wino Forever.”

Emilio Estevez

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The Breakfast Club actor was once engaged to this actress.

Demi Moore

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Moore and Estevez called off their engagement in 1986. Moore wed Bruce Willis the following year.

Evan Rachel Wood

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The Across the Universe actress was once engaged to this shock rocker.

Marilyn Manson

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Manson and Wood got together following Manson’s split from burlesque star Dita Von Teese. Manson popped the question in 2010, but the pair split seven months later.

Jennifer Lopez

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The “Booty” singer was set to wed this A-list actor.

Ben Affleck

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“Bennifer” was a tabloid obsession. The couple began dating in 2002 and were engaged two years later. The relationship ended in 2004, much to the disappointment of gossip mags everywhere.

Jude Law

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Law was engaged to his Alfie co-star until an affair ended their relationship.

Sienna Miller

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The pair met on the set of their film in 2003. They broke up two years later when Law confessed that he had an affair with his children’s nanny. Though the pair gave it another shot in 2011, the relationship ran its course.

Katie Holmes

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Before she wed Tom Cruise, Holmes was engaged to this actor.

Chris Klein

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The Just Friends actor and the Dawson’s Creek alum got engaged on Christmas of 2003, but broke up two years later.

Sheryl Crow

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The “All I Wanna Do” singer was engaged to this now-disgraced cyclist.

Lance Armstrong

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The one-time couple — who were both diagnosed with different forms of cancer around the same time — dated from 2003 to 2006 but never walked down the aisle.

Alison Pill

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The Newsroom actress recently called off her engagement to this actor.

Jay Baruchel

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The This Is The End actor was originally set to wed Pill in 2012, but the plans for their wedding kept getting pushed back. In 2013, they called off the wedding — and relationship — for good.

Laura Dern

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The Wild At Heart actress was dropped by her then-fiance when he met another woman on set.

Billy Bob Thornton

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Thornton dropped his fiancee Dern after meeting Angelina Jolie. Jolie became Thornton’s fifth wife, and Dern was left scratching her head.

Miley Cyrus

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Cyrus had barely completed her major makeover when she and her then-fiance called things off.

Liam Hemsworth

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The singer and the Hunger Games star called it quits in 2013 after meeting on set of their romantic drama The Last Song in 2009.

Nicole Richie

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The Candidly Nicole star is married to Good Charlotte rocker Joel Madden, but was once engaged to this DJ.


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Richie and DJ AM (real name Adam Goldstein) dated from 2003 and got engaged in 2005. In 2006, the couple called it quits. Sadly, DJ AM passed away four years later in 2010.

Alanis Morissette

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Believe it or not, the Canadian singer was once engaged to the star of the Green Lantern.

Ryan Reynolds

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Reynolds and Morissette got engaged in 2004 after two years together but broke up in 2007 before they could get hitched.

Kate Moss

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The supermodel was nearly wed to this rockstar.

Pete Doherty

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The Libertines frontman and the model met in 2005 and dated for two years before getting engaged, but the relationship ended before the couple could wed.

Jennifer Morrison

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The Once Upon A Time actress was once engaged to her House co-star.

Jesse Spencer

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Morrison and Spencer — who played love interests on their Fox show — met on the way to shoot the House pilot in 2004 and got engaged in 2006. Like their characters on the show, the two weren’t endgame, and broke up for good in 2007.