Inside Jake Gyllenhaal’s Long-Term Crush on Jennifer Aniston

Jake Gyllenhaal – currently riding the wave of Spider-Man: Far From Home’s glorious triumph – has been one of Hollywood’s most fascinating showbiz figures for quite some time. From Donnie Darko and Velvet Buzzsaw to The Prince of Persia and, most recently, Far From Home, his acting portfolio oozes with variation, as he works across big-budget and smaller, independent films alike. 

Jake Gyllenhaal and Jennifer Aniston
Jake Gyllenhaal and Jennifer Aniston | Photo by Jason Merritt/FilmMagic for Variety Magazine

When he met Jennifer Aniston, Gyllenhaal’s career was on the rise, as he had just recently starred in 2001’s Donnie Darko. However, Aniston had already cemented her career in Friends and was married to another Hollywood A-lister, Brad Pitt. Back in 2002, he was the newbie actor with feelings for the girl all of America had fallen in love with.

Gyllenhaal must have been quite the talented actor (on-screen and off), for he learned to hide his feelings from the taken celebrity. However, he later admitted to crushing on Aniston while filming 2002’s The Good Girl.  

‘Spider-Man: Far From Home’ star Jake Gyllenhaal on Jennifer Aniston 

In an interview back in 2016, Jake Gyllenhaal discussed working with Aniston. He explained to People Magazine:

“I will say, I had a crush on her for years. And working with her was not easy…I was – um, yeah. That’s all I’m going to say. It was lovely. It wasn’t hard, that’s what I would say.”

Gyllenhaal, tripping over his words a little bit, seems to fall back into his 2002 mental space almost immediately. Who knows, maybe he remembers his feelings from yesteryear and would like to give it a shot with the now-single actress. Too hopeful? Fans of these two can only dream. 

Jake Gyllenhaal also explained that it wasn’t just Friends that catalyzed his attraction to Jennifer Aniston; he told the interview that her “personality from afar” and other movies she had starred in played more significant roles in his blooming affection.

Only a charmer like Gyllenhaal would cite someone’s “personality from afar” as the basis of an attraction; could this get more Hollywood romantic? He also tells the interview that, after having a crush on Aniston for years, working with her did present a few difficulties. However, Jennifer Aniston clearly never knew.

Jennifer Aniston’s response to discovering that Jake Gyllenhaal had a crush on her 

During an interview with Access Hollywood, Jennifer Aniston was told, “Jake Gyllenhaal recently revealed that you were his all-time crush.” Aniston replied, “Well, I just don’t know why we’re finding this out now!”

Jennifer Aniston was then asked if things would have changed had she known earlier. She, with sincerity and humor, responded, “I don’t know,” before going on to explain that he must like “the older ladies.” Aniston also stated that Gyllenhaal definitely hid his attraction well, while on the set of The Good Girl. 

Considering Gyllenhaal and Aniston had to lock lips for The Good Girl, hiding his attraction must have been quite the challenge! However, like the gentleman fans know him to be, Gyllenhaal prevented the then-married actress from ever discovering how he felt; now, that’s what we mean by class.