38 Celebs You Totally Forgot Were Once Engaged

HOLLYWOOD - MARCH 23: (FILE PHOTO) Actors Ben Affleck and fiancee Jennifer Lopez attend the 75th Annual Academy Awards at the Kodak Theater on March 23, 2003 in Hollywood, California. Police in North Carolina have issued a warrant for the arrest of Ben Affleck after a woman claimed that he threatened to kill her. In a sworn statement in front of a magistrate the woman, Tara Ray, testified that Affleck had followed her home and communicated threats to her. Aflleck's spokesman called the allegation as absurd and defamatory. (Photo by Kevin Winter/Getty Images)
Source: Kevin Winter/Getty Images Entertainment/Getty Images

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

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

Gwyneth Paltrow

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

Kanye West

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

Amber Rose

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

Kiefer Sutherland

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

Julia Roberts

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

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

Michael Keaton

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

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

Carson Daly

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

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

Johnny Depp

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

The Breakfast Club actor was once engaged to this actress. 

Demi Moore

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

Evan Rachel Wood

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

Marilyn Manson

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

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

Ben Affleck

“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

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

Sienna Miller

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

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

Chris Klein

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

Sheryl Crow

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

Lance Armstrong

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

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

Jay Baruchel

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

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

Billy Bob Thornton

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

Miley Cyrus

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

Liam Hemsworth

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

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


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

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

Ryan Reynolds

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

Kate Moss

The supermodel was nearly wed to this rockstar. 

Pete Doherty

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

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

Jesse Spencer

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.