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Reese Witherspoon’s Dating History: Ryan Phillippe, Jake Gyllenhaal, Jim Toth and More of Her A-List Romances
25.03.2023 - 01:47 / usmagazine.com
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. They finalized their split in 2008.)
“It was funny — we were reminiscing then because we shot a lot of Cruel Intentions [here] … and [the kids] were tripping out on the fact that we were there shooting a movie before they were even a thought in our minds,” he told Huffington Post Live at the time, noting that the former spouses were in a “really great place” at the moment.
Still, the divorce took a toll on Witherspoon for some time.
“I spent a few years just trying to feel better,” the Oscar winner recalled to 60 Minutes in 2014. “You know, you can’t really be very creative when you feel like your brain is scrambled eggs. I was just kind of floundering career-wise cause I wasn’t making things I was passionate about, I was just kinda working. It was really clear the audiences weren’t
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