Ryan Gosling, Sandra Bullock(01 of21)
Open Image ModalRoger Ebert, Oprah Winfrey(02 of21)
Open Image ModalAndre Agassi, Brooke Shields(03 of21)
Open Image ModalNowadays, it's hard to imagine that one of the most high-profile couples in the '90s was tennis star Andre Agassi and actress Brooke Shields. The couple dated for six years before marrying in 1999; they divorced just two years later. (credit:Getty)
Lance Armstrong, Ashley Olsen(04 of21)
Open Image ModalGeorge Clooney, Talia Balsam(05 of21)
Open Image ModalCourteney Cox, Michael Keaton(06 of21)
Open Image ModalConan O'Brien, Lisa Kudrow(07 of21)
Open Image ModalSarah Jessica Parker, Robert Downey Jr.(08 of21)
Open Image ModalDrew Barrymore, David Arquette(09 of21)
Open Image ModalThese two Hollywood staples were briefly linked in 1991 -- eight years before they starred together in 1999's "Never Been Kissed." (credit:Getty)
Alanis Morissette, Ryan Reynolds(10 of21)
Open Image ModalCarson Daly, Tara Reid; Katie Holmes, Chris Kelin(11 of21)
Open Image ModalCutest -- and weirdest -- double date ever? Carson Daly/Tara Reid and Katie Holmes/Chris Klein are the epitome of the '90s here. (credit:Getty)
Moby, Natalie Portman(12 of21)
Open Image ModalJack Nicholson, Lara Flynn Boyle(13 of21)
Open Image ModalOwen Wilson, Sheryl Crow(14 of21)
Open Image ModalCameron Diaz, Matt Dillon(15 of21)
Open Image ModalThe telegenic "There's Something About Mary" co-stars dated for three years before splitting in 1998 -- the same year the hit comedy hit the big screen. (credit:Getty)
Macaulay Culkin, Mila Kunis(16 of21)
Open Image ModalSinitta, Simon Cowell(17 of21)
Open Image ModalMadonna, Dennis Rodman(18 of21)
Open Image ModalBilly Corgan, Tila Tequila(19 of21)
Open Image ModalThe romance between the Smashing Pumpkins frontman and reality star came out of nowhere, and left just as quickly as it arrived. (credit:Getty)
Shia LaBeouf, Hilary Duff(20 of21)
Open Image ModalEmma Stone, Kieran Culkin(21 of21)
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