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Reese Witherspoon’s Dating History: Ryan Phillippe, Jake Gyllenhaal, Jim Toth and More of Her A-List Romances

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Reese Witherspoon has been married to Ryan Phillippe and Jim Toth — see her star-studded dating history over the years
What, like it’s hard? 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 may have made fans swoon over Witherspoon and Phillippe’s characters at the time, but the Big Little Lies star later told Andy Cohen that her and Phillippe’s children — Ava, born in 1999, and son Deacon, born in 2003 — had absolutely no desire to watch the movie.
“They’re like, ‘This is so weird!’ And especially seeing me and their dad having sex. It’s so weird,” she told the Bravo host in 2015.
The Shooter alum, for his part, recalled going on a walk through Manhattan with Witherspoon and their children post-divorce. (The pair called it quits in 2006 after five years of marriage.

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