Gyllenhaal dated the “Bring It On” star, Kirsten Dunst, for just a little over two years. Dating someone for two years definitely counts as a serious relationship in our book.
While they both acted in Spiderman movies, Dunst was a part of the original movies with Tobey Maguire, and Jake played Mysterio in 2019’s “Spider-Man: Far from Home” with Tom Holland.
The actor must have a thing for singer-songwriters, as in 2001 when he was 21, he dated Jenny Lewis, who is known as the lead singer of indie band Rilo Kiley. She was just beginning her career, but the two were definitely a hot indie item.
Lewis is actually four years older than Jake and was 25 when they dated, we guess he has a thing for age gaps?
They Stayed Friends
Usually, when people break up they say that they'd love to remain friends, but most of the time, that's a blunt lie. It seems that Jenny and Jake took that sentence seriously...
Unlike some of his other notable exes, Lewis and Gyllenhaal remained friends. He took another girlfriend of his, one Reese Witherspoon, to see Lewis in concert. In 2011, ten years after they parted ways romantically, they even went to the Golden Globes together. Inspiring or weird? We'll let you decide...
They Adopted a Dog
Kirsten and Jake dated between 2002-2004 after meeting each other, how predictable, on a movie set. Jake's sister, Maggie had a part in the movie "Mona Lisa Smile." When Jake came to visit his sister, he met Dunst. The two became inseparable, they moved in together and adopted a dog.
They named their German Shepherd "Lovey." Cute? Or is it too on the nose? We'll let you be the judge of that.
She Dumped Him
It seemed the two had a nice thing going for them, so what happened? Rumor has it that in the end, it was actually Dunst who dumped Gyllenhaal in 2004 when they were both 22.
Except for the fact they were both very young and maybe didn't want to commit, what could have compelled her to say goodbye to someone who millions of fans consider to be "The perfect man"?