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  1. Nov 11, 2021 · Jake and Taylor dated for only three months in late 2010, breaking up just before the new year. Taylor had just turned 21 weeks before she and Jake broke up (though he seems to have missed her party, if "The Moment I Knew" is truly about him). At the time they split, Jake was 30.

    • Sara Belcher
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    • October 24, 2010: Taylor Swift and Jake Gyllenhaal Grab Brunch in Brooklyn
    • November 25, 2010: Taylor Swift and Jake Gyllenhaal Spend Thanksgiving Together
    • November 27, 2010: Taylor Swift and Jake Gyllenhaal Visit Nashville Together
    • December 10, 2010: Taylor Swift and Jake Gyllenhaal Drive Around Los Angeles
    • December 13, 2010: Taylor Swift Turns 21 and Celebrates Without Jake Gyllenhaal
    • January 4, 2011: Taylor Swift and Jake Gyllenhaal Split
    • October 22, 2012: Taylor Swift Releases Red
    • July 22, 2015: Jake Gyllenhaal Calls Taylor Swift A "Beautiful Girl"
    • September 19, 2017: Jake Gyllenhaal Smoothly Evades Questions About Taylor Swift

    The next morning, the pair were spotted getting brunchwith another couple at Al Di La in Brooklyn. An onlooker said they looked "friendly," and the two stars were then seen out for a stroll in Brooklyn's Park Slope neighborhood.

    The "Speak Now" singer was spotted with the Brokeback Mountain star early on Thanksgiving Day,stopping at Park Slope's Gorilla Coffee in Brooklyn around 10:30 a.m. for maple lattes. "They were really sweet, really really sweet," said a source at the shop. The actor's sister Maggie Gyllenhaallived nearby, and the pair were famously photographed hold...

    Two days after their Brooklyn coffee stop made headlines, the pair flew to Swift's hometown of Nashville together. There, they were spotted grabbing a late breakfast at Fido, another coffee shop. "They were smiling and laughing. They were talking a lot and enjoying each other's company," a source told PEOPLE. "They didn't look like [just] friends."

    ​​The next day, the lovebirds were seen on an afternoon drive through the city in Gyllenhaal's Audi. "Jake and Taylor seemed to be catching up and were chatting nonstop in the car," a source told PEOPLE. "Jake was making Taylor laugh and she looked very happy."

    The singer threw herself a Christmas-themed birthday partyat home in Hendersonville, Tennessee, to ring in her milestone birthday — which Gyllenhaal did not attend. The actor's no-show is largely thought to have inspired Swift's song, "The Moment I Knew," and the lyrics in her re-recorded, 10-minute version of "All Too Well:" "You, who charmed my d...

    "They're over," a source told PEOPLE at the start of 2011, confirming that the brief romance between the stars "ended last month." While the exact timing of their breakup isn't known, the former pair spent the holidays, as well as their December birthdays, apart.

    Swift released her fourth studio album in October 2012, which featured tracks that were largely interpreted by fans to be inspired by her breakup with Gyllenhaal. "All Too Well" struck a particular chord, with fans scouring the heartbreaking lyrics for details that could connect the actor to the song. One line from the track became something of Swi...

    During an appearance on Howard Stern's SiriusXM Radio Show, Gyllenhaal was once again nudged on the topic of his brief relationship with Swift. In response to Stern saying that he was "super attracted" to the singer and that Gyllenhaal should have married her, the actor replied, "She's a beautiful girl." Gyllenhaal then played coy when Stern sugges...

    During a Q&A with Boston Marathon bombing survivor Jeff Bauman — whom Gyllenhaal portrayed in the film Stronger —the actor once again proved his prowess in avoiding the subject of Swift. "If you lost your legs in real life, do you think Taylor Swiftwould write a song about it?" Bauman, who lost his legs in the attack, asked Gyllenhaal. "Like a coun...

    • Sophie Dodd
  3. Nov 12, 2021 · At the time of their split, Gyllenhaal was 30-years-old, while Swift was 21 — a nine-year age difference. A source close to the actor also spoke to Us Weekly, stating, "Jake cares about...

  4. Nov 12, 2021 · They had a 9-year age gap as Swift was 21 and Gyllenhaal was 29 when they were together, which may have been one of the reasons why Gyllenhaal called it quits on their relationship.

  5. Feb 17, 2022 · Swift and Gyllenhaal began dating when she was 19 and he was 28. When they broke up, she was 20 to his 29. The age difference matches that of Dylan O'Brien and Sadie Sink, who star in the short...

  6. Nov 12, 2021 · Taylor Swift’s ‘All Too Well (10 Min.)’ Reveals Jake Gyllenhaal Blamed Breakup On Age Difference. The ten minute version of 'All Too Well' paints a fuller picture of Taylor Swift...

  7. Nov 15, 2021 · Let's be clear: It's legal for a 29-year-old to date a 20-year-old. The oldest age of consent set by any U.S. state is 18. But just because something is legal doesn't mean it's ethical. For some...

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