38 of 60
Reese Witherspoon & Ryan Phillippe
Set Where They Met: "Cruel Intentions," in which his character tries to seduce her character. They actually met at a party before filming.
Relationship Status: Divorced after eight years of marriage. They have a daughter, Ava, and son, Deacon, together.
Repeat Offender(s): Post-divorce, Witherspoon later dated her "Rendition" co-star Jake Gyllenhaal (and then they broke up), while Phillippe was seeing Australian actress Abbie Cornish, whom he met on "Stop-Loss." She was supposedly the "other woman" who wrecked his marriage.