Love and Other Drugs Director Challenged Jake Gyllenhaal to Try 'Hitting on Women' to Prepare for Role

Jake Gyllenhaal put his rizz to the test after director Ed Zwick challenged him while preparing for his Love and Other Drugs role.

Zwick’s new memoir Hits, Flops, and Other Illusions: My Fortysomething Years reveals how the director, 71, helped get Gyllenhaal, 43, into character.

In the 2010 rom-com with Anne Hathaway, Gyllenhaal played womanizing Viagra salesman Jamie. “His job as a salesman takes second place to his vocation, which is hitting on women. That wasn’t Jake’s style at all,” Zwick writes, adding, "Not to say he didn’t do just fine with women ... but his 'game' wasn’t overt." He explained that the Brokeback Mountain star’s charm lied in his “innate authenticity.” 

When Zwick noticed Gyllenhaal eyeing a woman at dinner, he urged him to get her number, the director said. After an initial refusal, the director managed to convince the star to approach her. He later returned with a grin and a number, scribbled on a napkin.

Back in 2010, Gyllenhaal told Huffington Post how he related to his Love and Other Drugs character.

"Part of my job is a little bit of that. I've gotta be a salesman. There's a nature to the act — there's a real performance — and there's a real performance to sales, so I think as an actor, it's natural," he said at the time, adding, "What I love about Jamie is his sense of performance. ... A real sense of being able to walk into a room and have so much confidence that people would trust whatever he said. That was really wonderful to play, because I haven't played anything like that before."

In the memoir, though the director denies implying that the spontaneous flirting heavily influenced Gyllenhaal’s performance on-screen, Zwick does note that the star was “damn good” in scenes where he seduces Hathaway’s character.

Off-handedly, Zwick added that, at the film’s London premiere, Gyllenhaal introduced his new girlfriend at the time, Taylor Swift. “I’m just sayin’...” Zwick wrote.

Swift, now 34, and Gyllenhaal dated briefly at the end of 2010. The stars first sparked romance rumors when they were spotted backstage at Saturday Night Live on an episode hosted by Swift’s friend Emma Stone. They later spent time together in Brooklyn, Nashville and during Thanksgiving. At the start of 2011, a source confirmed to PEOPLE that the couple had broken up.

The singer’s relationship with Gyllenhaal is speculated to have inspired her 2012 album Red, and nine years later, serve as the source for her Billboard Hot 100 No. 1 song “All Too Well (10 Minute Version) (Taylor’s Version).” 

In 2022, the Road House actor, who is now dating French model Jeanne Cadieu, denied the theories that the song had anything to do with their relationship. "It's about her relationship with her fans. It is her expression. Artists tap into personal experiences for inspiration, and I don't begrudge anyone that,” he told Esquire. 

Hits, Flops, and Other Illusions: My Fortysomething Years is available now wherever books are sold.