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There may be a short list of stars who've stood the test of time together, even in Hollywood, but not all celebrity unions are meant to last. Remember when Jennifer Aniston dated Tate Donovan and Penélope Cruz went out with Tom Cruise? How about Rachel Bilson's relationship with Adam Brody, or the time Alanis Morissette was engaged to Ryan Reynolds? Scroll through to see those duos and more surprising celebrity couples!

Adam Brody and Rachel Bilson
Cameron Diaz and Matt Dillon
Jack Nicholson and Lara Flynn Boyle
Josh Groban and January Jones
Salma Hayek and Edward Norton
Jennifer Lopez and Diddy
Kristen Johnston and Ryan Reynolds
Jennifer Esposito and Bradley Cooper
Emma Stone and Kieran Culkin
Gwen Stefani and Tony Kanal
Brooke Shields and Andre Agassi
Kate Hudson and Alex Rodriguez
Sarah Jessica Parker and Robert Downey Jr.
Julia Roberts and Lyle Lovett
Katie Holmes and Chris Klein
Alanis Morissette and Ryan Reynolds
Kelly Preston and George Clooney
Penelope Cruz and Tom Cruise
Lance Armstrong and Sheryl Crow
Jennifer Lopez and Wesley Snipes
Helen Hunt and Hank Azaria
Julia Roberts and Kiefer Sutherland
Alyssa Milano and Scott Wolf
Mila Kunis and Macaulay Caulkin
John Krasinski and Rashida Jones
Ashley Judd and Michael Bolton
Heather Graham and Heath Ledger
Christina Applegate and Brad Pitt
Megan Fox and David Gallagher
Busy Philipps and Colin Hanks
Jennifer Aniston and Tate Donovan
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