40 Celebrity Couples You Forgot Dated In The Early ’00s
Natalie Portman and Jake Gyllenhaal
Jake Gyllenhaal was a certified hottie in the ’00s, so he played the field a bit following his split with Kirsten Dunst. Jake and Natalie Portman are good friends to this day (he once called her “the Audrey Hepburn of our generation” at the Desert Palm Achievement Awards), but they likely dated in 2002 and possibly gave it another try in 2006. Jake has joked that it’s impossible to pick a restaurant because of Natalie’s veganism, but if that was the main issue, being vegan is super in since the late 2010s, so it’d probably be easier for the couple to find a place to eat nowadays.