Reese Witherspoon & Chris O’Donnell – 1993
Reese Witherspoon became a household name in the acting scene when she starred in Legally Blonde and Cruel Intentions. You might think actor Ryan Phillippe was her first famous partner, but she briefly dated Chris O-Donnell during the ’90s.
There is not much information available about their relationship, but it looks like they only dated for less than a year. Witherspoon’s marriage to Ryan Phillippe lasted from 1999 until 2007, and her current husband is Jim Toth. O’Donnell was the more fortunate one because his marriage with Carolina Fentress has been smooth sailing since 1997.
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