From Ryan Phillippe to Jake Gyllenhaal: Inside Reese Witherspoon's relationships.

From her iconic role in Legally Blonde to her appearance in hit TV drama Big Little Lies, Reese Witherspoon has graced our screens for over 20 years. But it was her role in 90s cult classic Cruel Intentions that first shone a spotlight on her.

The hit 1999 romance film catapulted the young actress to fame and gave her the chance to work alongside her then-partner, Ryan Phillippe.

The couple, who played Sebastian Valmont and Annette Hargrove in the film, proved they had more than on-screen chemistry and went on to marry shortly after.

Alas, as is the way with young Hollywood couples, the pair eventually went their separate ways, with Witherspoon pursuing relationships with other famous names in the industry.


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