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 made fans swoon over Witherspoon and Phillippe’s connection both on and off screen.

Witherspoon and Phillippe wed in 1999 and later welcomed two children, Ava, born in 1999, and son Deacon, born in 2003. After getting divorced in 2006 — which was finalized two years later — the Legally Blonde actress was linked to several more Hollywood hotties, including Jake Gyllenhaal.

Witherspoon gave marriage a second shot in 2011 when she said “I do” to publicist Jim Toth. The pair welcomed son Tennessee in 2012, but after more than a decade together they divorced in 2023.

Scroll down to see Witherspoon’s complete dating history: