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Sarah Jessica Parker & Robert Downey Jr.
Before she wed Matthew Broderick, the Sex and the City alum was going steady with the Avengers star. Before they ended their seven-year romance in 1991, they attended the 1990 MTV VMAs together.
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Jeff Kravitz/FilmMagic
Brad Pitt & Christina Applegate
As the story goes, these two went on one date and chose the 1989 MTV VMAs as the setting. However, she left mid-date for a mystery man and the two never went out again.