Revisiting Reese Witherspoon's Star-Studded Dating History: Ryan Phillippe, Jake Gyllenhaal and More

Look back at Reese Witherspoon's confirmed and rumored dating history, which includes actors Ryan Phillippe and Jake Gyllenhaal and more of her past co-stars.

By Corinne Heller Dec 30, 2020 6:52 PMTags
Watch: Reese Witherspoon Reacts to Ryan Phillippe's 2002 Oscars Moment

Reese Witherspoon brought back major nostalgic vibes when she mentioned her ex-husband Ryan Phillippe on a podcast.

On The HFPA in Conversation, host and journalist Margaret Gardiner asked the actress about the time she and the actor co-presented an award at the 2002 Oscars, during which he said she should speak before him because she makes more money than him. Reese said in the interview that the moment "wasn't scripted" and she did not know he would say it ahead of time.

"There's so few women that make a lot of money that sometimes they're shamed for it, and sometimes they are expected to give more and do more and be more to others in the same position that, say, a male movie star would not be expected to," Reese said. "But I do think gender norms have changed quite a bit since that moment in 2000 or something."

They Dated? Surprising Star Couples

Reese, 44, and Ryan, 46, co-starred in the dark teen cult film Cruel Intentions and were married between 1999, the year the film was released, and 2008. The actors, once one of the most popular celebrity couples, share two children, Ava Phillippe, 21, and Deacon Phillippe, 17.

Three years after her divorce from Ryan, Reese married her current husband, CAA talent agent Jim Toth. The two share a son, Tennessee Toth, 8.

But Ryan is not the first actor Reese has dated. In the past, she has also been romantically linked to more of her co-stars, including Jake Gyllenhaal. Check out her confirmed and rumored dating history below:

Chris O'Donnell: Just Rumors

The two were romantically linked in 1993 after the actress, then 16 years old, accompanied the then-22-year-old actor to a tribute party for his Scent of a Woman co-star Al Pacino in New York City. Neither Reese nor Chris ever confirmed a relationship.

Stephen Dorff: Just Rumors

The two starred in the 1994 movie S.F.W. (which stands for "So F--king What") and sparked dating rumors in the early '90s. "I wouldn't date Dorff for all the money in the world," Reese told Details magazine in 1995. "I really admire the girls who do hold Dorff's attention. I don't know if it's because he doesn't know what he wants, or that he knows exactly what he wants and if that person doesn't apply, he's going to find it somewhere else. You have to be comfortable giving him space. I'm not that kind of girl."

Mark Wahlberg: Just Rumors

Mark and Reese sparked romance rumors after showcasing chemistry in the 1995 thriller Fear. Neither has ever confirmed a relationship.

Jake Gyllenhaal: Dated

The two co-starred in the 2007 thriller Rendition and dated for two years before they split in 2009.

"He's very supportive," Reese told Vogue in 2008. "Suffice it to say, I'm very happy in life, and I'm very lucky to have a lot of really supportive people around me who care very much for me, and, you know, that's all you can hope for in life. I am very blessed in that way."

Ryan Phillippe: Married and Divorced

Despite popular belief, the two did not meet on the set of the 1999 film Cruel Intentions, in which they played love interests. Reese and Ryan actually first met when he crashed her 21st birthday party in 1997, weeks before the actor got the script for the movie. The two kept in touch after the bash and he immediately passed the screenplay to her after he received it, according to Pennsylvania newspaper The Morning Call.

"I crashed her party," Ryan told the outlet in 1999. "I went with a friend because I knew there would be free food and drinks. I was just sitting back in the corner pounding away the drinks when somebody walked over and introduced Reese to me."

Reese told Jane magazine in 1998, "I don't know what came over me—maybe the seven Midori sours—but I told him, 'I think you're my birthday present.' He thought it was so flattering, and now that I think about embarrassing!"

The two wed in June 1999, three months after the release of Cruel Intentions, and are parents to daughter Ava Phillippe, born in 1999, and Deacon Phillippe, born in 2003. Reese and Ryan finalized their divorce in 2008.

Jim Toth: Married

Reese and Jim, a CAA talent agent, tied the knot in 2011 after dating for a year. The two welcomed son Tennessee Toth in 2012 and are still happily married.