In 2011 Jake was in a brief relationship with Jenny Lewis.

They broke up within months but stayed good friends.

Jake dated Kirsten Dunst from 2002 to 2004. They met through his sister!

Reese Witherspoon, third girlfriend, couldn’t commit to Jake Gyllenhaal.

Jake dated a very famous singer Taylor swift, but they breakup due to age gap!

Jake finally found his true love in Jeanne; they started dating 2018.