Looking Back On Jake Gyllenhaal’s Stacked Dating History On The Anniversary Of His Infamous Maple Latte Date With Taylor Swift

“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.”

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.  

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