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These stars were actually got engaged before they separate!

Ouch!

Emilio Estevez And Demi Moore

Photo by Ron Galella, Ltd./WireImage

Emilio Estevez and Demi Moore met on the set of St. Elmo’s Fire. They started a romantic relationship and even got engaged. In 1987, they broke off their engagement. Shortly after that, Demi Moore started dating her future husband, Bruce Willis.

Then they got divorced and she married Ashton Kutcher, and then they got divorced.

Marilyn Manson And Evan Rachel Wood

Photo by Eric Charbonneau/WireImage for Disney Pictures
Marilyn Manson and Evan Rachel Wood got engaged in 2010, but they split up later that year.

At first this pairing seems a bit odd, but when you think about it, Marilyn Manson is pretty much a normal dude under all that makeup, and Evan Rachel Wood has a bit of a wild side.

Courteney Cox And Michael Keaton

Photo by Jim Smeal/WireImage
Courteney Cox and Michael Keaton were together from 1989 – 1995. Their relationship predates Friends and lasted until the first season of the show started airing. At the time, neither Courteney nor Michael knew how big the show was going to be.

They didn’t end up getting married, but they were engaged for a while.

Kiefer Sutherland And Julia Roberts

Photo by Ron Galella, Ltd./WireImage
Kiefer Sutherland and Julia Roberts were engaged in the early 1990s, but Julia called off the wedding just a few days before it was supposed to take place. Maybe she should have starred in Runaway Bride.

Oh wait, she did. Well, that makes sense.

Amber Rose And Kanye West

Photo by Pascal Le Segretain/Getty Images
Before Kaye married Kim Kardashian, he was engaged to Amber Rose. Actually, before he was engaged to Amber Rose, he was engaged to designer Alexis Phifer.

Kim’s had her share of failed relationships too, so I guess now they’re even? Amber Rose is doing just fine.

Kate Moss And Pete Doherty

Photo by Phillip Massey/FilmMagic
Model Kate Moss and the Libertines frontman Pete Doherty were briefly engaged in 2007. After his engagement to Moss, Doherty was briefly engaged to model Irina Lăzăreanu.

Doherty definitely has a thing for models. Unfortunately, he couldn’t make any of those relationships stick. As far as I know, Kate Moss is also single at the moment.

Alanis Morisette And Ryan Reynolds

Photo by Frazer Harrison/Getty Images
You oughta know that Alanis Morisette and Ryan Reynolds were an item from 2002 to 2007. They were even engaged, but they called off their engagement before they ever got married.

It’s hard to imagine Ryan Reynolds with anyone other than Blake Lively. Alanis has also found a husband, so everybody is doing just fine.

Heather Locklear And Jack Wagner

Photo by Samir Hussein/Getty Images for FitFlop Shooting Stars Benefit
Jack Wagner and Heather Locklear met on the set of Melrose Place. They didn’t start dating until years after the show ended, though. They began a relationship in 2007, right after Locklear’s second divorce was finalized.

They got engaged in August of 2011, but called off the engagement just a few months later.

Jennifer Lopez And Ben Affleck

Photo by Barry Chin/The Boston Globe via Getty Images
Sometimes it’s easy to forget tha Ben Affleck and J.Lo were the original Bennifer. These two were a thing, and very few of us were into it. I don’t even think J.Lo was into it, and if she was, she’s not into it anymore.

They got engaged in 2002, but a year later they called it quits.

Carson Daly And Tara Reid

Photo by Jeff Kravitz/FilmMagic
Carson Daly and Tara Ried together are what ’90s dreams are made of. Just saying their names take me back to the days of Slinkies and Sony Walkmen.

Carson proposed to Tara in October of 2000, but by the summer of 2001, they had called off the wedding.

Billy Bob Thornton And Laura Dern

Photo by Ron Galella/WireImage
Billy Bob Thornton and Laura Dern were engaged in 2000. Billy Bob has actually been married six times and divorced five, so luckily this relationship ended before they made things legal. Seven marriages would just be too much.

Thornton married Angelina Jolie shortly after breaking up with Laura Dern.

Jude Law And Sienna Miller

Photo by Stephen Lovekin/Getty Images
Sienna Miller and Jude Law almost got married in the mid 2000s, but they called the whole thing off after Sienna discovered that Jude was having an affair with his children’s nanny.

Even though they called off the wedding, they still continued to date until 2011.

Katie Holmes And Chris Klein

Photo by Chris Polk/FilmMagic
American Pie actor Chris Klein was engaged to Katie Holmes in 2003. The couple called off their engagement and ended their relationship in 2005. Klein went on to marry a travel agent named Laina Rose Thyfault. They have two children together.

Katie Holmes went on to marry Tom Cruise, and we all know how that went.

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