"I love love, man."

Jake Gyllenhaal said this in an interview with Howard Stern back in 2015, and when you look at his dating history over the years, it's pretty easy to confirm that the Hollywood star does, in fact, love love.

He's been in several high-profile relationships—some serious, some not-so-serious—but has always remained fiercely private when it comes to his personal life. 

"I'm not necessarily guarded, but I consider intimacy to be very important and I don't think everybody needs to know about my family or my personal details," he said in an interview with The Guardian in 2017. "I'm old school in that way." And when asked about his personal life, specifically if he is playing with fire by dating famous women, he simply explained, "I would love to not talk about my personal life."

Still, that hasn't stopped the public from being oh-so-very interested in his dating life, especially when you realize he's never actually settled down despite being in several longterm relationships. 

At 37, Gyllenhaal has never been married, and he was pretty candid when talking about the subject during the chat with Stern. 

"I think I probably just got scared," he said of never walking down the aisle with his previous girlfriends. "There are a lot of beautiful women, there are opportunities, but I think at the same time, if you find the right person, I believe in monogamy I believe in when you meet somebody who is right it will be right and you will stay there."

Jake Gyllenhaal, Cannes

George Pimental

At the time, Gyllenhaal was single, and admitted he wasn't happy about it and said he does "hope" he will eventually get married. 

And while he didn't name the two women, the Nocturnal Animals star did reveal he's been in love "twice." 

Given his surprisingly impressive dating history, speculation quickly began over which two girlfriends Gyllenhaal had really been in love with. To properly investigate, we decided to look back on all of his relationships (even rumored ones), including his infamous fling with Taylor Swift, which felt appropriate given that the two were spotted on their iconic maple latte date eight years ago today.  

Jake Gyllenhaal, Jenny Lewis, 2011 Golden Globes


Kirsten Dunst, Jake Gyllenhaal

Splash News

Kirsten Dunst, Jesse Plemons, 2018 Emmys, 2018 Emmy Awards, Couples

John Shearer/Getty Images

Jake Gyllenhaal, Natalie Portman, Odd Couple

Kevin Mazur/WireImage.com

Reese Witherspoon, Jake Gyllenhaal

Frazer Harrison/Getty Images

Reese Witherspoon, Jim Toth, 2017 Oscars, Vanity Fair After Party

PA/PA Images via Getty Images

Taylor Swift, Jake Gyllenhaal


Taylor Swift, Jake Gyllenhaal


Taylor Swift, Joe Alwyn

Jackson Lee / SplashNews.com

Anna Kendrick, Jake Gyllenhaal

Kevin Winter/Getty Images

Jessica Lowndes

John Sciulli/Getty Images for Louis XIII

Minka Kelly, Jake Gyllenhaal

Getty Images

Jake Gyllenhaal, Emily DiDonato

Henry S. Dziekan III/Getty Images; MARK RALSTON/AFP/Getty Images

Jake Gyllenhaal, Alyssa Miller


Jake Gylennhaal, Southpaw


Jake Gyllenhaal, Ruth Wilson

Elder Ordonez/INFphoto.com

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