Inside Reese Witherspoon And Jake Gyllenhaal's Relationship

When it comes to celebrity relationships, some of them truly do make it for the long haul. Others aren't quite so lucky — and, unfortunately for Reese Witherspoon and Jake Gyllenhaal, they landed in the unlucky category. 

It's possible that you entirely forgot that the two actors even dated, but they did indeed date for a couple of years. According to InStyle, the two met in 2006 on the set of "Rendition." While Witherspoon and Gyllenhaal technically met on the film's set in Morocco, they apparently didn't spend much time together during that period. During the film's reshoots in LA, however, Gyllenhaal reintroduced himself, and things grew from there.

Witherspoon was fresh off of a separation from Ryan Phillippe, and interestingly enough, Gyllenhaal was an "old workout buddy" of Phillippe (via People). Despite having ties to her ex, Gyllenhaal pursued Witherspoon, and over time, she reciprocated feelings as well. "Things slowly progressed, but it was never something she thought would happen from the start. She just kind of developed this little crush over time," a friend of Witherspoon's explained to People at the time.

For about two years after their initial connection, Witherspoon and Gyllenhaal would date off and on — let's take a closer look inside their relationship!

When Jake Gyllenhaal and Reese Witherspoon first connected on the set of "Rendition," there was no way of telling just how much the two actors would eventually hit it off. While it did prove true that Gyllenhaal and Witherspoon had an undeniable connection, their relationship would be anything but smooth sailing. 

The two started dating sometime in 2006, though Witherspoon was still dealing with her separation from Ryan Phillippe at the time. By summer of 2007, Witherspoon apparently pulled the plug on her relationship with Gyllenhaal, and the fact that she was fresh off of a marriage had a lot to do with it. "She just got out of a divorce and was so concerned with her family, she just didn't have the time for him and he really demanded that," a source explained to People about the breakup. 

Eventually, however, Witherspoon came around, and that same year, she and Gyllenhaal got back together. The actor's divorce from Phillippe would be finalized in 2008, making it much easier to move forward with Gyllenhaal and open up to a new relationship.

Though Reese Witherspoon and Jake Gyllenhaal did break up shortly after they started dating in 2007, once they got back together, they were going stronger than ever. 

According to People, Gyllenhaal was possibly hearing wedding bells in the relationship — but Witherspoon didn't feel the same way. "As much as everyone thinks they're right there, they're really not near the whole marriage thing," a source explained about the couple in 2008. "Jake would marry her tomorrow, but Reese doesn't want to go there yet, even though he would like to." The source explained that while the duo had become a "team," Witherspoon was really happy with her life at the time and didn't want to "screw that up."

Though Witherspoon didn't share Gyllenhaal's feelings about marriage, it doesn't mean she wasn't pretty smitten with her then-beau. In a 2008 interview with Vogue, the actor gave a rare insight into her relationship. "He's very supportive," she said of Gyllenhaal, via People. "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."

While Reese Witherspoon and Jake Gyllenhaal were one of Hollywood's hottest couples at one point, their relationship would ultimately come to an end. "It broke his heart," an insider explained to Us Weekly about the couple's 2009 breakup. "She couldn't give Jake enough and she got cold feet. Jake wanted all of her." Apparently, Witherspoon was also concerned about Gyllenhaal's capacity to be a stepfather to her two children: "He was great with the kids, but she felt like he didn't get the whole scope of what that entailed," a source explained. 

Though things were slightly messy when they first broke up, it's safe to say that Gyllenhaal hasn't harbored any bad feelings about Witherspoon. In 2016, seven years after the couple called it quits, Gyllenhaal reminisced about his ex. "She is, as I would say about most of the women who I'm close friends with or had relationships in my life, one of the smartest, strongest people I've ever met," the actor gushed during an episode of "The Jess Cagle Interview," via People. 

Clearly, there was no bad blood between the former golden couple. Many people were rooting for them to possibly even marry some day, but it simply wasn't in the cards. Witherspoon did eventually find lasting love with husband Jim Toth, and Gyllenhaal has been dating French model Jeanne Cadieu since 2018 (via Elle).