Ryan Phillippe, her co-star in 1999's Cruel Intentions, was the only Hollywood heartthrob on Witherspoon's agenda for most of her 20s. The couple married in 1999 and had two children together, Ava, now 13, and Deacon, 9. Unfortunately, the couple divorced in 2007, amidst rumors Phillippe cheated.
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Witherspoon's next tabloid-frenzy relationship came six months later when she began dating her Rendition co-star Jake Gyllenhaal. The famous duo stayed together for nearly three years, until their relationship hit a critical "get engaged or break up" point, and we all know what road she took.
A mere two months later, the Oscar winning actress started seeing CAA agent Jim Toth, who would ultimately become hubby #2 in March 2011. In September 2012, they welcomed their first child together, son Tennessee James.
In light of her 37th birthday on March 22, here are 5 things you may have missed about her love life over the years:
Did you say couple's therapy? Witherspoon admitted to attending couples' therapy while still married to Ryan Phillippe. "It's always struck me as odd that people grabbed onto that story and made it sound so negative. In what capacity is working on yourself or your marriage a bad thing? What marriage isn't a journey? If you don't have money to go to therapy, there's always church. You can get together with groups and friends and talk about things with other couples," she says.
Is she the jealous type? Witherspoon first met Phillippe at her 21st birthday party and the two then co-starred in Cruel Intentions. "I had to see him make out with a lot of really cute chicks," she told Entertainment Weekly. "That was definitely difficult."
Girls only. There was no kissing behind the bleachers in high school for Witherspoon. The straight-A student attended Harpeth Hall, an all-girls school in Nashville. "I really believe in single-sex education," she told People in 2002.
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Her first kiss. Although we don't officially know who Witherspoon smooched first off-screen, she puckered up before the cameras for the first time at age 14 when she swapped tongues with co-star Jason London in 1991's The Man in the Moon. Keep reading ...
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