Colin Farrell, Elizabeth Taylor(01 of56)
Open Image ModalSharon Osbourne, Jay Leno(02 of56)
Open Image ModalJessica Simpson, Jensen Ackles(03 of56)
Open Image ModalPenelope Cruz, Josh Hartnett(04 of56)
Open Image ModalParis Hilton, Val Kilmer(05 of56)
Open Image ModalWinona Ryder, Charlie Sheen(06 of56)
Open Image ModalJennifer Love Hewitt, Fred Savage(07 of56)
Open Image ModalCher, Tom Cruise(08 of56)
Open Image ModalHelen Hunt, Matthew Broderick(09 of56)
Open Image ModalPamela Anderson, Michael Jackson(10 of56)
Open Image ModalEvan Rachel Wood, Marilyn Manson(11 of56)
Open Image ModalFrank Sinatra, Mia Farrow(12 of56)
Open Image ModalJonny Lee Miller, Angelina Jolie(13 of56)
Open Image ModalKiefer Sutherland, Julia Roberts(14 of56)
Open Image ModalRyan Gosling, Rachel McAdams(15 of56)
Open Image ModalLyle Lovett, Julia Roberts(16 of56)
Open Image ModalBrooke Shields, Nicolas Cage(17 of56)
Open Image ModalNot much is known about their relationship, but somewhere in the late '80s, Shields and Cage dated for about a year. (credit:Getty)
Winona Ryder, Jimmy Fallon(18 of56)
Open Image ModalLance Armstrong, Ashley Olsen(19 of56)
Open Image ModalJohn Tesh, Oprah Winfrey(20 of56)
Open Image ModalGary Oldman, Uma Thurman(21 of56)
Open Image ModalGeorge Clooney, Talia Balsam(22 of56)
Open Image ModalConan O'Brien, Lisa Kudrow(23 of56)
Open Image ModalJohnny Depp, Ellen Barkin(24 of56)
Open Image ModalCourteney Cox, Michael Keaton(25 of56)
Open Image ModalRyan Gosling, Sandra Bullock(26 of56)
Open Image ModalDrew Barrymore, David Arquette(27 of56)
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)
Drew Barrymore, Tom Green(28 of56)
Open Image ModalSarah Jessica Parker, Robert Downey Jr.(29 of56)
Open Image ModalMoby, Natalie Portman(30 of56)
Open Image ModalAshton Kutcher, January Jones(31 of56)
Open Image ModalOwen Wilson, Sheryl Crow(32 of56)
Open Image ModalAl Pacino, Diane Keaton(33 of56)
Open Image ModalKeaton dated her "Godfather" co-star Al Pacino in the '80s; the relationship dissolved after Keaton pushed a marriage ultimatum on Pacino. She told People: "He's charming, hilarious, a nonstop talker. There was an aspect of him that was like a lost orphan, like this kind of crazy idiot savant. And oh, gorgeous! I was mad for him. I worked hard on that one." (credit:Getty)
Josh Hutcherson, Vanessa Hudgens(34 of56)
Open Image ModalJack Nicholson, Lara Flynn Boyle(35 of56)
Open Image ModalEmilio Estevez, Demi Moore(36 of56)
Open Image ModalCameron Diaz, Matt Dillon(37 of56)
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)
Enrique Iglesias, Sofia Vergara(38 of56)
Open Image ModalShia LaBeouf, Hilary Duff(39 of56)
Open Image ModalAaron Carter, Lindsay Lohan(40 of56)
Open Image ModalEmma Stone, Kieran Culkin(41 of56)
Open Image ModalJohn Stamos, Marlee Matlin(42 of56)
Open Image ModalSeal, Tyra Banks(43 of56)
Open Image ModalSeal sure has a thing for telegenic supermodels! Seal and Tyra confirmed their budding romance when they stepped out to the Essence Awards in 1996, but broke up shortly thereafter. (credit:Getty)
Whoopi Goldberg, Ted Danson(44 of56)
Open Image ModalJake Gylenhaal, Natalie Portman(45 of56)
Open Image ModalCarson Daly, Tara Reid; Katie Holmes, Chris Kelin(46 of56)
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)
Matthew Morrison, Kristen Bell(47 of56)
Open Image ModalMinka Kelly, Donald Faison(48 of56)
Open Image ModalBefore she got together with Yankees star Derek Jeter, Kelly dated the "Clueless" actor for a year, from 2004-2005. (credit:Getty)
Avril Lavigne, Brody Jenner(49 of56)
Open Image ModalBrad Pitt, Robin Givens(50 of56)
Open Image ModalChristina Applegate, Brad Pitt(51 of56)
Open Image ModalThe Brad strikes again: This time, with the "Married with Children" actress in 1988. (credit:Getty)
Richie Sambora, Cher(52 of56)
Open Image ModalCher was involved with the Bon Jovi guitarist for two years in the early '90s. We bet the glamour-hair contests were awesome. (credit:Getty)
Sinitta, Simon Cowell(53 of56)
Open Image ModalMadonna, Dennis Rodman(54 of56)
Open Image ModalKelly Preston, Charlie Sheen(55 of56)
Open Image ModalJennifer Lopez, Ben Affleck(56 of56)
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