Maggie and Jake Gyllenhaal ..Here's a fun fact: This pair are the first and only brother-sister duo to be nominated for Academy Awards in the 21st century; she for best supporting actress in 2009's Crazy Heart and he for best supporting actor in 2005's Brokeback Mountain. Those Gyllenhaals are a loving and talented bunch!
Kirsten Dunst and Jake Gyllenhaal How long it lasted: 2 years What it FELT like in our heads: In perpetuity These indie darlings began dating in 2002 after Jake Gyllenhaal's older sister, Maggie Gyllenhaal, introduced them. (Maggie and Kirsten Dunst worked together on the film Mona Lisa Smile.) The cute couple even shared a home in L.A. and adopted a dog, but they ended up splitting in 2004. At least, we'll forever have these photos of them eating.
Pics: Shirtless Jake Gyllenhaal Makes a Sexy Splash on the Beach With Maggie!