#13: Minnie Driver and Matt Damon

Duration of Relationship: Less than a year (1997–1998)

Minnie Driver and Matt Damon’s breakup in 1998 became infamous after Damon announced it publicly during an interview on The Oprah Winfrey Show, much to Driver’s surprise. The pair had fallen in love while filming Good Will Hunting, and their chemistry on-screen seemed to translate into real life.

However, things took a turn when Damon, seemingly out of the blue, declared he was single on national television. Driver later expressed shock and disappointment, noting that the split was unexpected. Their breakup became a pop culture moment, highlighting the often messy intersection of personal relationships and public life in Hollywood.