Gyllenhaal briefly dated actress Natalie Portman in 2006. While introducing Portman at the 2011 Palm Springs Film Festival, Gyllenhaal revealed he met the actress at a Star Wars convention when he approached her to sign his Queen Amidala doll.
According to E! News, the two were initially romantically linked back in 2002 but didn't make headlines until 2006, when they were spotted out on a date. It's unknown how long their romance lasted, but it was brief.
Despite their romance fizzling out, the two remained friends over the years and worked together on the 2009 film "Brothers." Gyllenhaal joked in his 2011 Palm Springs Film Festival speech that Portman's veganism made dating difficult, saying, "It does get hard when you're out to dinner with her."