In 2001, the starlet was back at the show, that time with a new rock star.
While their relationship lasted less than a year, this duo managed to hit the 2008 MTV VMAs red carpet together before their split two months later.
Before she embarked on a 20-year-long marriage (and counting) to Matthew Broderick, the Sex and the City alum was going steady with the Avengers star between 1984 and 1991. They attended the 1990 MTV VMAs together.
As the story reportedly 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.