Taylor Swift and Jake Gyllenhaal first met through Gwyneth Paltrow and Chris Martin. "I've just known Jake for a long time and he's a great guy," said Paltrow in a December 2010 interview. "And Chris (Martin, Paltrow's former husband) has a friendship with Taylor."

They got closer to each other by October 23, 2010, when Swift and Gyllenhaal stopped by "Saturday Night Live" in support of that night's host, one of Swift's closest friends, Emma Stone. Swift and Gyllenhaal followed the hangout session with a lunch date in Brooklyn, where they were also joined by Stone. Shortly after that first sighting, Swift sat down with Ellen DeGeneres and danced around the rumors, saying only, "I'm always optimistic about love."

The exchange that followed included DeGeneres giving Swift her unsolicited seal of approval. "It's just y'all hanging out -- this does not prove anything," DeGeneres said after displaying a photo of the two out in public. "I'm just saying he's adorable, and I like him very much, and so if that is the case that he's your boyfriend, I think that's fantastic."

Then in early November, Jake and Taylor were spotted in Big Sur, California, lounging by a pool and getting sundaes at McConnell's ice cream shop. One source said, "Taylor laughed at everything Jake said," and added that the pair seemed "happy" and "friendly."

What initially appeared to be a casual fling seemed to heat up as rumors hit the internet in mid-November that Gyllenhaal had rented a private jet to fly Swift out to the U.K. to hang out while he promoted "Love and Other Drugs." That date, however, was far more costly than a few scoops of ice cream as it reportedly cost the Hollywood heartthrob more than $150,000. Still, Gyllenhaal's "Other Drugs" co-star Anne Hathaway brushed off the romance rumors.

For Thanksgiving, Taylor and Jake returned to Brooklyn, where they spent the weekend visiting Jake's sister, Maggie Gyllenhaal and her husband, Peter Sarsgaard. Maggie later said spending the holiday with Swift was "great." The new couple then headed to Nashville, where they were repeatedly spotted, yes, getting coffee and strolling arm in arm.

Sources told Us Weekly at the time that the romance was heating up and that "she loves his family, and he loves hers." Later, during an interview, Swift gave a review of Gyllenhaal's latest flick, describing "Love and Other Drugs" as "a good movie." When pressed for more details about Jake, she said, "I write in great detail about my personal life, but I don't talk about it."

In January 4, 2011, came reports that the pair were no longer together. According to People, Gyllenhaal and Swift split up in December 2010. "They're over," a source told the mag about the short-lived relationship. "It ended last month." Mere weeks after news spread that Taylor Swift and Jake Gyllenhaal had split up, comes word that the two were spotted out together again in Nashville on January 19, 2011.

People reports that Jake visited Taylor in Nashville where she lives. The duo were seen grabbing food at a restaurant, Bound'ry, on Wednesday, near the country superstar's condo. A patron tells the website that they ate alone at a table for two. "They did eat," the patron told People. "They were cordial to one another, but not affectionate."

Swift released her fourth studio album "Red" in late 2012. The album is full of songs about her on-again, off-again relationship with Gyllenhaal. "State of Grace," "Red," "All Too Well," "I Almost Do" and the infamous "We Are Never Ever Getting Back Together" are rumoured to be about Gyllenhaal.

According to sources, their relationship went downhill for the first time because Jake didn't attend Taylor's 21st birthday party and she "spent the night crying in the bathroom because Gyllenhaal told her that he would be there, but he didn't come." Red's bonus track "The Moment I Knew" seemingly confirmed these rumors. While talking about this song in particular, Swift said, "'The Moment I Knew' was a song about my 21st birthday party, which was the worst experience ever."

Besides "The Moment I Knew", another obvious song to be about Jake is "All Too Well" where Swift finds herself reminiscing on the memories of a past relationship from beginning to end. During the song, Swift mentions the fact that Gyllenhaal kept an old scarf that Taylor was wearing when she spent Thanksgiving with him. There are several photos of Taylor and Jake wearing the same scarf back then. With heartbroken lyrics and also teary eyes whenever she sings the song live, Swift mentioned the fact that she lost her virginity to Gyllenhaal, "After plaid shirt days and nights when you made me your own/Now you mail back my things and I walk home alone/But you keep my old scarf from that very first week/'Cause it reminds you of innocence and it smells like me."

In one of her speeches before singing the song in her Red Tour in 2013, Swift said, "When I'm writing songs, I think for me my main goal is to write exactly what I'm feeling, when I'm feeling it. If writing songs happens for me in the middle of the night, say between the hours of 2 and 4 am, chances are, I'm trying to forget somebody. It's almost impossible to write how you feel. If you've ever lost somebody, you know that you're never just feeling one feeling at a time. It's much more complicated than that and when I was writing my song, I decided maybe instead of writing how I felt, maybe it would be better to write what happened from beginning to end because, I remember it all too well."

In 2021, Swift released her re-recorded version of Red, including other songs that are assumed to be about her relationship with Jake - songs she wrote back in 2011, but didn't make it to the Red original 2012 album, like "Babe," "Better Man," "I Bet You Think About Me," and an extended version of "All Too Well." Swift also directed and produced a short film for "All Too Well" starring actors Sadie Sink and Dylan O'Brien.