THE ARTISTREE  PRESENTS

JAKE GYLLENHAAL DATING HISTORY

JAKE GYLLENHAAL AND KIRSTEN DUST

Early in his career, Early in his career, Jake Gyllenhaal was in a relationship with Kirsten Dunst.

JAKE GYLLENHAAL AND NATALIE PORTMAN

They were first linked in 2002 and were spotted on a date in 2006. Despite their on-off romantic history, the two have maintained their friendship.

Jake Gyllenhaal AND Reese Witherspoon

The couple first met on the set of the thriller "Rendition" in 2006 during reshoots in Los Angeles

Prior to their relationship, Witherspoon was married to actor Ryan Phillippe, with whom she shares two children. They separated in 2007. 

Despite their on-off romantic history, the two have maintained their friendship.

JAKE GYLLENHAAL AND TAYLOR SWIFT

Jake Gyllenhaal and Taylor Swift began dating in late 2010, though their romance fizzled out just before New Year's. When Jake broke up with her.

Swift has written about their whirlwind relationship on hit songs like "All Too Well" and "We Are Never Ever Getting Back Together."

JAKE GYLLENHAAL AND JESSICA LOWNDES

Months after his split with  Taylor Swift, Jake got back with Jessica Lowndes in April 2011.

JAKE GYLLENHAAL AND MINKA KELLY

Minka Kelly has reportedly had a secret hook-up with Jake Gyllenhaal.

Kelly had turned Gyllenhaal down when he first asked her out last fall. But later, Kelly “decided to give Gyllenhaal another chance.” But they didn’t hit it off.

JAKE GYLLENHAAL AND ALYSSA MILLER

Going to the gym has its benefits! Jake began dating Alyssa Miller after first meeting at their New York City gym in June 2013.

JAKE GYLLENHAAL AND JEANNE CADIEU

In December 2018 Jake sparked a romance with the French model Jeanne Cadieu

She and Jake really took things slow, but are now pretty serious. The couple have kept their relationship relatively private but were spotted together in Los Angeles in June 2020, proving their flame hadn't fizzled out.