Ryan Phillippe
Then: Though he made his career debut in I Know What You Did Last Summer, Ryan Phillippe really stole our hearts as bad boy Sebastian in Cruel Intentions, where he met future (ex) wife Reese Witherspoon. The two were married for 7 years, and have 2 kids together. Phillippe went on to have a successful film and TV career, and has won a number of notable awards.
Now: This year Phillippe will star in the ABC drama Secrets and Lies, an adaptation of the Australian series, as a murder suspect. He’s been happily dating law student Paulina Slagter since 2011.
[Photos via @ryanphillippe and @ryanphillippe]
[Photos via @ryanphillippe and @ryanphillippe]
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