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So many ex-fiancés in Hollywood.
by Lauren YapalaterBuzzFeed Staff
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1. Jennifer Aniston and Tate Donovan got engaged in 1998.
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They ended things shortly after, but he had already committed to filming his guest role on Friends as Josh-u-ah, so they ended up filming it having literally just broken up.
Ron Galella, Ltd. / Ron Galella Collection via Getty Images
2. Tate Donovan was also engaged to Sandra Bullock at some point during their relationship that started in 1990.
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They ended it all in 1994.
Ron Galella / Ron Galella Collection via Getty Images
3. Jeffrey Dean Morgan and Mary-Louise Parker got engaged sometime in late 2007-ish.
Barry King / WireImage
They split up in April of 2008.
Christopher Polk / WireImage
4. Laura Dern was engaged to Billy Bob Thornton during their relationship from 1997-1999.
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Their relationship ended when Billy Bob literally just started a relationship with Angelina Jolie and then married her while Laura was away working on a movie!!!! He never even broke up with her!!!!! Absolutely nuts.
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5. Laura Dern was also engaged to Jeff Goldblum. They got engaged in 1995.
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They ended up breaking up in 1997.
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6. Rashida Jones and Mark Ronson were engaged in 2003.
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They broke up a year later. ¯\_(ツ)_/¯
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7. Rhys Ifans (who now plays Otto Hightower on House of the Dragon) and Sienna Miller were engaged in 2007.
Kevin Mazur / WireImage
They broke up in 2008.
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8. Lea Thompson and Dennis Quaid were engaged in 1984.
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They stayed engaged until they broke up in 1987.
Ron Galella / Ron Galella Collection via Getty Images
9. Julia Roberts and Dylan McDermott were engaged in 1989/1990.
Steve.granitz / WireImage
Apparently, she ended their engagement to date Kiefer Sutherland.
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10. Which brings me to Julia Roberts and Kiefer Sutherland getting engaged in 1990.
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They broke up lit'rally three days before their wedding in June 1991.
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11. Minnie Driver and Josh Brolin got engaged in 2001.
Jeff Kravitz / FilmMagic, Inc
They ended their engagement five months later.
Frank Trapper / Corbis via Getty Images
12. Chrishell Stause and Matthew Morrison got engaged in 2007.
Robin Platzer / FilmMagic
They ended their engagement later that year.
Theo Wargo
13. David Moscow and Kerry Washington got engaged in 2004.
Steve Granitz / WireImage
The engagement lasted until 2007, and then, they split up.
Denise Truscello / WireImage
14. Robin Wright and Ben Foster got engaged in 2014.
Christopher Polk / Getty Images for AFI
They ended up breaking up in 2015.
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15. Magician David Copperfield and supermodel Claudia Schiffer were engaged sometime in 2004-ish.
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The never got married, and broke up in 1999.
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16. Katie Holmes and Chris Klein got engaged in 2003.
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They ended the engagement and relationship in 2005. Then came Tom Cruise :).
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17. Ben Stiller and Jeanne Tripplehorn got engaged in 1993.
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They were engaged until they broke up in 1996.
Jim Smeal / Ron Galella Collection via Getty Images
18. Ryan Reynolds and Alanis Morissette got engaged in 2004.
Gregory Pace / FilmMagic
They ended the engagement and broke up in 2006.
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19. Cameron Diaz and Jared Leto allegedly got engaged in 2000.
Jeff Kravitz / FilmMagic
Their relationship ended in 2003, though, without a wedding.
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20. Emilio Estevez and Demi Moore got engaged in 1984.
Ron Galella, Ltd. / Ron Galella Collection via Getty Images
They broke up in 1987 when Demi indefinitely postponed the wedding because Emilio was caught cheating.
Ron Galella, Ltd. / Ron Galella Collection via Getty Images
21. Kyle MacLachlan and Linda Evangelista got engaged sometime around 1995.
Ron Galella, Ltd. / Ron Galella Collection via Getty Images
They never got married, and ended things in 1998.
Ron Galella, Ltd. / Ron Galella Collection via Getty Images
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