Reese Witherspoon has romanced multiple A-listers throughout her time in the spotlight, but not all of her relationships have had happily ever afters. After meeting Ryan Phillippe at her 21st birthday party in 1997, the twosome starred as love interests in 1999’s Cruel Intentions. The sexy flick made fans swoon over Witherspoon and Phillippe’s connection both on and off screen. Witherspoon and Phillippe wed in 1999 and later welcomed two children, Ava, born in 1999, and son Deacon, born in 2003. After getting divorced in 2006 — which was finalized two years later — the Legally Blonde actress w...

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