10 Things You Didn’t Know About Taylor Swift And Jake Gyllenhaal’s Relationship


Taylor Swift and Jake Gyllenhall’s relationship only lasted for about two to three months back in late 2010 but, in spite of this, most of us still remember it, probably because it had “disaster” written all over it from the beginning. He was nine years her senior, about to enter his thirties, and she was just 20 years old and romantically inexperienced when they dated, which in and of itself was a pretty big red flag. Even though these two obviously weren’t meant to be, we figured it might be fun to reminisce about the days when Taylor and Jake were one of Hollywood’s hottest couples:

10. First Date

For one of their first dates, they went apple picking at the Fishkill Farms in Hopewell Junction, N.Y. Some of the customers tried to take photos with them, but they hid in the trees to avoid them. At this point, they had only been dating two to three weeks tops and no one was sure who pursued who, except that they both seemed pretty into each other.

Source: www.lifeandstylemag.com

9. He Was Looking to Settle Down

After they were first spotted on a date, a source told Hollywood Life that Jake was looking to settle down when he met Taylor. After dating Hollywood knockouts like Kirsten Dunst and Reese Witherspoon, he was finally ready for marriage and children. Lucky for him, Taylor was in the same mindset.

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8. He Pursued Her

A source told Us Weekly that the Brokeback Mountain actor asked his team for an introduction to the singer. All sources agree, from the start, he was the one pursuing her. It certainly helped that she had a thing for older men and then began to develop serious feelings for good old Jake.

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7. She Spent Thanksgiving with Him and His Sister Maggie

Swift spent thanksgiving with Jake and his sister Maggie and her family in 2010. The once happy couple were spotted walking arm in arm around Brooklyn’s Park Slope neighborhood where Maggie lives. Sources told Us Weekly at the time that the romance was heating up and that “she loves his family, and he loves hers.”


6. Gwyneth Paltrow, The Matchmaker

Gwyneth Paltrow is the one who introduced Jakey to Swifty! She admitted that they met at one of her dinner parties at her London home to USA Today. According to her, she and Jake have been close friends since they co-starred in the 2005 drama Proof and Taylor has a friendship with her husband at the time, Chris Martin.

Malcolm Taylor/Everett Collection

5. He Did The Dumping

Even though he was the one who pursued her, the Nightcrawler actor was also the one who ended the relationship with the award-winning songstress right before New Years Ever after only a few months of dating. He reportedly dumped her via phone – just like Joe Jonas did. She was devastated by the sudden breakup and stopped eating and started hitting up the gym to exercise her sadness out.

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4. He Wasn’t Happy with the Media Attention

One of the big reasons that Gyllenhall ended the relationship with Swift was because of the media attention. He wasn’t comfortable with all of the attention that they received and wanted to maintain a certain level of privacy. He also became less comfortable with their age difference, which became more apparent the more they continued to date.


3. Post Breakup Meeting

In January 2011, the former couple was spotted at Bound’ry, a restaurant near Swift’s Nashville condo, having a meal together. Although they weren’t affectionate, it led many to think that they might get back together. A source close to Taylor claimed that he wanted to see if they could recapture the magic, but it wasn’t there. The meeting was more or less for closure.

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2. Vanity Fair Oscar Party Confrontation

A few months after their breakup, Taylor and Jake ran into each other at the Vanity Fair Oscar Party. “They were outside near the restroom having a discussion,” a guest at the Vanity Fair party told People. “It seemed a bit more serious – it certainly wasn’t a ‘Hi, how are you?’ talk.” There was reportedly no overt affection between the two. It just looked like they were sorting something out.

Photo by Peter Brooker / Rex Features

1. They Are Never Ever Getting Back Together

Like with all of her breakups, Swifty let her emotions about Jake out in her music. Her song “We Are Never Ever Getting Back Together” is about their relationship. An insider told Hot Stuff that it is “definitely about Jake” and Swift explained in an interview with Nightline that her inspiration for the song came after one of her ex boyfriend’s friends came and told her that he heard she and her ex were getting back together. “When he leaves, Max and Johan are like, ‘So what’s the story behind that?’ And so I start telling them the story of break up, get back together, break up, get back together, just, ugh, the worst,” she said.



Cate has a B.A. and an M.A. in English Literature and has been the Managing Editor of Fame10 for more than 6 years. Despite having a love for the works of Thomas Hardy, Leo Tolstoy and Lord Byron, she also has an intense fascination with pop culture. When she isn’t writing for Fame10, she’s planning her next big adventure in Southeast Asia.