Who: Shooter star Ryan Phillippe, 44, and Oscar-winning actress, acclaimed producer, and entrepreneur Reese Witherspoon, 42.
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How They Met: Reese and Ryan met in 1997 at the actress’s 21st birthday party. “I don’t know what came over me — maybe the seven Midori sours — but I told [Ryan], ‘I think you’re my birthday present,’” Reese admitted to Jane magazine in 1998. “He thought it was so flattering, and now that I think about it … how embarrassing!”
A year after their fateful meeting, the duo got engaged. Before they could make it official, Reese became pregnant with her and Ryan’s first child. In 1999, just three months after the premiere of their soon-to-be cult classic Cruel Intentions, Reese and Ryan tied the knot during a romantic ceremony in Charleston, South Carolina. Three months into their wedded bliss, the actors welcomed a daughter, Ava. Four years later they welcomed a son, Deacon.
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Thinking back a lot this summer. ☀️ Remembering when these two were little and all the fun summer trips! ❤️ #MarthasVineyard #FBF
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me n mine ?
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Why We Loved Them: Has a more perfect-looking couple every existed? No wonder they had kids so young — can you imagine looking like this and not feeling the urge to procreate as soon as humanly possible? Had they stayed together and had 10-20 more children, Reese and Ryan may have created a race of straight-up models.
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When They Peaked: Sebastian Valmont and Annette Hargrove will forever be our everything.
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The Breakup: Reese and Ryan both agree that they were just too young when they started dating.
In 2015, Ryan told Larry King he thought age was to blame for his 2007 divorce. “I think more of the problem was age. When we got together we were so young,” he explained. “I think it can create issues with two people in this industry because there’s so much noise that goes along with it.”
Reese echoed his sentiment during an interview with ITV’s Lorraine in 2017. “I got married when I was 23 and I had two kids by the time I was 27. So I don’t know, you know, sometimes it’s good to know yourself,” Witherspoon shared. “I would never change anything,” she continued, explaining, “I’ve said to my daughter, I think, you know, [at] 25, you start to know yourself a little bit better.”
Aside from their respective ages, Phillippe has long been rumored to have begun an affair with Stop-Loss co-star Abbie Cornish while on set (and still married to Witherspoon) in 2006.
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Where They Are Now:
Phillippe and Cornish dated until early 2010. After their split, Ryan had a summer fling with then 21-year-old actress and model Alexis Knapp, who gave birth to her first (and Ryan’s third) child, a daughter named Kai, in the summer of 2011. Phillippe spent the next 5 years with girlfriend (and eventual fiancée) Paulina Slagter before breaking off the engagement in late 2016.
Professionally, Phillippe’s seen success with USA drama Shooter, which aired its final episode earlier this month.
In 2011, Reese wed her talent agent boyfriend Jim Toth. The following year they welcomed a son, Tennessee, who celebrates his sixth birthday later this month.
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Happy birthday to the best husband, friend, and father in the world !! I love you JT. ❤️?✨( and you make me laugh EVERYday! ?what’s better than that?!)
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This boy I tell ya… #SweetSummertime
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In 2012, Reese founded production company Pacific Standard, which is now a subsidiary of her 2016 media company Hello Sunshine. The actress has since produced and/or starred in several films (Wild, Gone Girl, Hot Pursuit) and HBO hit series Big Little Lies.
The year after launching her production company, Reese embarked on a clothing and lifestyle brand called Draper James.
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We're giving our mamas an extra tight squeeze today and hope y’all are too! Happy Mother's Day!
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Oh, and then she wrote a book:
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New York City I love you!! So excited to be here celebrating #WhiskeyInATeacup and kicking off my book tour tonight! I can't believe my book comes out tomorrow! ?☕️ (photo @kdeenihan) #NYC
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What can’t this woman do?
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