Brad Pitt courtship: 1989
Actress Christina Applegate (a.k.a. Kelly Bundy on "Married with Children") briefly dated Brad Pitt when she was a household name — and he wasn't. She has said she "ditched him" at the 1989 MTV Video Music Awards and left with someone else. Here the duo appear together at that show.
For more stories about celebrity families and relationships, read:
The Ex Files: The Girlfriends of George Clooney
Top 10 Midlife Marriages of 2011
Longest Celebrity Marriages
Shortest Celebrity Marriages
Famous Weddings from the Past
Once Was Not Enough: These Celebrities Married Multiple Times
Famous Estrangements (Part 1)
Famous Estrangements (Part 2)