Reese Witherspoon’s Love Life: From Ryan Phillippe To Jim Toth

As the actress announces her engagement, we review her dating history.

Reese Witherspoon joined an ever-growing list of engaged celebrities Tuesday when she announced that she and boyfriend Jim Toth plan to tie the knot . Over the course of her public life, Witherspoon has been married once before (to Ryan Phillippe) and even dated Jake Gyllenhaal for quite a bit of time. With congratulatory wishes to Witherspoon and Toth, we take a look back at Witherspoon’s dating history.

(Check out photos of Reese with her past loves.)

Before meeting and marrying Phillippe, Witherspoon had been romantically linked to Jason London, Stephen Dorff, Chris O’Donnell and Mark Wahlberg, but it was Phillippe who Witherspoon settled down with for about a decade.

As the story goes, Phillippe arrived to Witherspoon’s 21st birthday party in 1997, where love bloomed. The “Cruel Intentions” co-stars got engaged in December 1998 and married in June 1999. The pair quickly started a family with the arrival of their daughter, Ava, in September of that year. Four years later, they welcomed their son, Deacon, in October 2003.

Before they split in 2006, Witherspoon opened up about married life, noting that it wasn’t always easy. Revealing that she and Phillippe went to couple’s therapy, she said, “We’ve done that in the past, and it’s always struck me as odd that people grabbed onto that story and made it sound so negative. In what capacity is working on yourself or your marriage a bad thing? What marriage isn’t a journey? If you don’t have money to go to therapy, there’s always church. You can get together with groups and friends and talk about things with other couples.”

After divorcing Phillippe in 2007, Witherspoon was spotted with her “Rendition” co-star Jake Gyllenhaal. The two tried to keep their relationship quiet, but after being photographed together multiple times, it was Phillippe who let the cat out of the bag. “It’s bizarre,” he told USA Today in March 2008 of seeing photos of the couple.

Witherspoon herself eventually confirmed the relationship to Vogue in October of that year, calling Gyllenhaal “very supportive.”

“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,” she said. “I am very blessed in that way.”

But the couple was broken up by November 2009. After several months alone, Witherspoon began dating talent agent Jim Toth in February 2010. The pair’s announcement of their engagement Tuesday comes after nearly a year of dating.

Witherspoon opened up to Glamour about being in a relationship with someone who’s not a celebrity, saying, “I have a little perspective on this. I wouldn’t say it’s easier. Every relationship has its own dynamic. And I don’t want to disparage any of the other relationships that I’ve had that were meaningful and wonderful. But what I’m finding out is that it’s very comfortable to be with somebody who understands my career, but doesn’t do what I do. He’s a great guy. He’s wonderful.”

Send your well-wishes to Witherspoon and Toth in the comments section below!