Reese Witherspoon's Dating History: Ryan Phillippe, Jim Toth and More

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:

Before her romance with Phillippe, Witherspoon was one-half of another iconic ‘90s couple while dating Clueless star Sisto.

“[Reese] was my first actress girlfriend,” the Waitress actor recalled during a 2015 Reddit AMA, revealing the two hit it off while working on a 1992 TV movie. “We had a long-distance relationship for a long time,” he shared, gushing, “I was so into her.”

Sparks flew when the I Know What You Did Last Summer star met Witherspoon at her 21st birthday party in 1997. The next few years were golden for the then-couple, who starred alongside each other in 1999's Cruel Intentions, got engaged — and married! — and welcomed their first-born, daughter Ava. Deacon joined the family four years later. Seven years after they wed, the pair split amid rumors that Phillippe was cheating on the Man in the Moon star with Abbie Cornish, whom he went on to date. (The Locksmith star denied the cheating allegations.)

“We are saddened to announce that Reese and Ryan have decided to formally separate,” a rep for the actors said at the time. “They remain committed to their family and we ask that you please respect their privacy and the safety of their children at this time.” They finalized their divorce in 2008. Despite their personal turmoil, Witherspoon and Phillippe remain dedicated coparents to their children.

Witherspoon began dating Gyllenhaal in 2006 while working together on the movie Rendition. After the Election star ended their three-year relationship in 2009, a source exclusively told Us that there was nothing significant that caused their split. "No one cheated," a source told Us. "There was no drama."

One year after her split from Gyllenhaal, Witherspoon began dating Toth. Their relationship quickly progressed, tying the knot in 2011 and welcoming son Tennessee one year later.

In 2013, however, Witherspoon made headlines for her uncharacteristic behavior when she was arrested for disorderly conduct and Toth for a DUI. The actress asked the police officer if he knew her name, per the police report at the time. Witherspoon later apologized for her behavior in a statement to Us.

Toth, who was driving the car, was sentenced to community service, one year of probation and an alcohol education program after pleading guilty. Witherspoon, for her part, pleaded no contest to disorderly conduct and was ordered to pay a fine.

While the couple’s only headlines throughout the next decade were sweet ones, Toth and Witherspoon announced the end of their marriage in March 2023.

“It is with a great deal of care and consideration that we have made the difficult decision to divorce,” they wrote via social media. “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 former couple 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.”

Witherspoon and Toth finalized their divorce in August 2023. The duo signed a marriage dissolution agreement and agreed to a parenting plan for son Tennessee.

Witherspoon was linked to Haarmann in July 2024 after spending time in New York City. Us confirmed in September of that year that the actress was officially dating the German financier after growing close as friends. In July 2025, the couple were spotted packing on the PDA while summering in France together.