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The Good Will Hunting co-stars had a very public breakup back in 1998.
The talented twosome dated briefly in the late-nineties but ultimately called it quits in 2000.
The Beetlejuice actor and Friends star dated from 1989 to 1995.
The Charmed actress and Scream star dated in 1991.
The actors began dating in 1990 after co-starring in Flatliners. They announced their engagement in August and planned to marry on June 14, 1991. However, Roberts called off her wedding to Sutherland three days before it was scheduled to take place.
The pair dated briefly in 1996 following Roberts' guest appearance on Friends.
The pair dated from 1998 to 2001.
After meeting on the set of Made in America in 1993, Goldberg and Danson dated briefly. During a 2015 appearance on Bravo's Watch What Happens Live!, the View co-host joked she'd "bone so many people" since dating Danson.
The future Oscar winner briefly dated the New Kids on the Block singer in 1990.
The singer-actress briefly dated the former NBA star in 1994.
The unlikely duo dated for about eight months in 1991.
The HIMYM star dated the actress (and future wife of Ben Stiller) in 1997. "She's the coolest, nicest chick ever. She's an absolute catch," Harris, who is married to David Burtka, later revealed in an interview with Howard Stern. "And I thought, 'If I'm not going to feel the super sparks with her... it probably means I'm gay."
The Something About Mary co-stars dated from 1995 to 1998.
The Two and a Half Men star and Mad Men actress dated from 1998 to 2001.
The former pair dated from 1997 to 2000.
The actor and supermodel were married from 1991 to 1995.
The model-actress and NBA player were married briefly in 1998.