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Slide 21 of 49

Reese Witherspoon and Ryan Phillippe

In 1997, Ryan attended a party in honour of Reese's 21st birthday. They reportedly spent all night talking to each other, and Reese made the first move. "I don't know what came over me — maybe the seven Midori sours — but I told him, 'I think you're my birthday present.'" OK, best line ever. They started dating, starred as an onscreen couple in Cruel Intentions, and tied the knot in 1999 while Reese was six months pregnant with the couple's daughter, Ava. Reese filed for divorce in 2006, but we'll always have the iconic romance between Annette Hargrove and Sebastian Valmont to look back on.

Image Source: Getty / Steve.Granitz