Matt Damon and Winona Ryder - Gwyneth Paltrow allegedly introduced the pair in 1997, they dated for two years and even went to the Golden Globes together. (Photo by LUCY NICHOLSON/AFP/Getty Images)
Nick Cannon and Kim Kardashian - Were together for a few months in 2006 but he ended it after she lied about her sex tape. (Photo by Ethan Miller/Getty Images)
Cameron Diaz and Robbie Williams - Had a short lived romance in the summer of 2003. Weirdly she told Robbie to get back with his wife years later when he was in rehab. (Photos by Stuart C. Wilson/Getty Images & Eamonn McCormack/Getty Images)
Michael Keaton & Courtney Cox - Were together for six years but split in 1995. (Photos by Christopher Polk/Getty Images & John Sciulli/Getty Images)
Tom Jones and Cher - Dated for a few months in the 80s when he was 23 and she was 39, she said he was 'shy' but she was 'crazy about him'. (Photos by Kevin Winter/Getty Images & Michael Buckner/Getty Images)
Ryan Reynolds and Alanis Morissette - The pair were together for five years and even got engaged but split up in 2007, though they remain good friends (Photo by Kevin Winter/Getty Images)
Sofia Vergara and Craig David - Briefly dated for a few months in 2003. (Photos by Frederick M. Brown/Getty Images & Martin Grimes/Getty Images)
Leonardo DiCaprio and Naomi Campbell - Had a fling in 1995 but decided they were better off as friends. (Photos by Frazer Harrison/Getty Images & Pascal Le Segretain/Getty Images)
Zooey Deschanel and Jason Schwartzman - He was her first real boyfriend when they got together at 19. (Photo by Evan Agostini/Getty Images)
Janet Jackson and Mathew McConaughey - Met at the 2002 Grammy Awards and kept their fling a secret.(Photo by HECTOR MATA/AFP/Getty Images)
Brad Pitt and Sinitta - Dated for two years back in the late 80s after she split up with Simon Cowell. (Photos by Tim P. Whitby/Getty Images & Ian Gavan/Getty Images)
Justin Timberlake and Fergie - Dated back in 1996 when she was 23 and he was 16, 'before he got real heavy with Britney' - Fergie. (Photo by Frank Micelotta/Getty Images)
Matthew Perry and Lizzy Caplan - Were together for six years and apparently split because he didn't want to get married. (Photos by Dimitrios Kambouris/Getty Images & Alberto E. Rodriguez/Getty Images)
Drew Barrmore and David Arquette - They dated when they were teenagers and he later described her as one of the sweetest people in Hollwood. (Photos by Frederick M. Brown/Getty Images & Michael Buckner/Getty Images)
Josh Groban and January Jones - Were together for over two years and Groban said it was his longest relationship. (Photo by Amanda Edwards/Getty Images)
Milo Ventimiglia and Alexis Bledel - Dated whilst filming Gilmore Girls, she's also rumoured to have dated her other co-star Jared Padalecki. (Photo by Kevin Winter/Getty Images)
Emily VanCamp and Chris Pratt - Met while filming US TV series Everwood but split in 2007. (Photo by Ethan Miller/Getty Images for CineVegas)
Rashida Jones and Tobey Maguire - Were an item just before Tobey's career took off with Spiderman. They were even rumoured to be engaged. (Photos by Ethan Miller/Getty Images and Jemal Countess/Getty Images)
Cameron Diaz and Jared Leto - Were together for four years from 1999 but kept their relationship very private. (Photos by Theo Wargo/Getty Images & Stephen Lovekin/Getty Images)
Tyra Banks and Seal - The pair secretly dated in 1996 before he got together with other supermodel Heidi Klum. (Photos by Jason Merritt/Getty Images & David Becker/Getty Images)
Helen Mirren and Liam Neeson - Met while filming Excalibur in Ireland in 1980 and dated for four years before they were well known stars. (Photos by Francois Durand/Getty Images & Alberto E. Rodriguez/Getty Images)
Robert Downey Jr and Sarah Jessica Parker - Were together from 1984 to 1991 but his drink and drug problems caused the split. (Photos by Ian Gavan/Getty Images & Neilson Barnard/Getty Images)
Dannii Minogue and Simon Cowell - Had a fling whilst they were judges on The X Factor, Cowell said he felt 'like a schoolboy' around her but they never went public (Photo by WENN.com)
Celebrities You Never Knew Dated
