A-List Romances of Reese Witherspoon: From Ryan Phillippe to Jake Gyllenhaal and Jim Toth

What, like it’s hard? 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 may have made fans swoon over Witherspoon and Phillippe’s characters at the time, but the Big Little Lies star later told Andy Cohen that her and Phillippe’s children — Ava, born in 1999, and son Deacon, born in 2003 — had absolutely no desire to watch the movie.

“They’re like, ‘This is so weird!’ And especially seeing me and their dad having sex. It’s so weird,” she told the Bravo host in 2015.

The Shooter alum, for his part, recalled going on a walk through Manhattan with Witherspoon and their children post-divorce. (The pair called it quits in 2006 after five years of marriage. They finalized their split in 2008.)

“It was funny — we were reminiscing then because we shot a lot of Cruel Intentions [here] … and [the kids] were tripping out on the fact that we were there shooting a movie before they were even a thought in our minds,” he told Huffington Post Live at the time, noting that the former spouses were in a “really great place” at the moment.

“I spent a few years just trying to feel better,” the Oscar winner recalled to 60 Minutes in 2014. “You know, you can’t really be very creative when you feel like your brain is scrambled eggs. I was just kind of floundering career-wise cause I wasn’t making things I was passionate about, I was just kinda working. It was really clear the audiences weren’t responding to anything I was putting out there.”

However, she soon moved on with publicist Jim Toth, whom she wed in 2011. Witherspoon and Toth welcomed their son, Tennessee, the following year.

With the exception of their highly-publicized arrest in 2013 — during which Toth was booked for a DUI and Witherspoon was handcuffed for disorderly conduct — the Wild actress and her husband enjoyed a low-key romance for more than a decade. In March 2023, however, the pair announced their split.

“It is with a great deal of care and consideration that we have made the difficult decision to divorce,” the estranged couple shared via social media at the time. “We have enjoyed so many wonderful years together and are moving forward with deep love, kindness and mutual respect for everything we have created together.”

The exes added: “Our biggest priority is our son and our entire family as we navigate this next chapter. These matters are never easy and are extremely personal. We truly appreciate everyone’s respect for our family’s privacy at this time.”