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After Kirsten Dunst, Jake Gyllenhaal moved on with another A-lister at the top of her ’00s fame: Reese Witherspoon. According to People, the actors had known one another for years, as Gyllenhaal was reportedly a “workout buddy” of Witherspoon’s ex-husband Ryan Phillippe, but it wasn’t until reshoots on their movie “Rendition” that the two got closer. “Things slowly progressed, but it was never something she thought would happen from the start,” a source told the outlet in early 2007. “She just kind of developed this little crush over time.”
In 2008, Witherspoon opened up about her relationship to Vogue after being pressed for details. “He’s very supportive,” she allowed. “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.”
Gyllenhaal moved in with her in 2008. They attended Coachella together and accompanied one another to various red carpets, with Gyllenhaal even reportedly growing close to her children. However, they split the following year. A source told Us Weekly that Gyllenhaal was ready to settle down, but apparently, Witherspoon’s divorce was still too fresh for her to be able to commit. “She felt pressured to wed again but she wasn’t ready,” the source said. “She couldn’t give Jake enough and she got cold feet. Jake wanted all of her.”
