When researching for our Jake episode for Red Week, the timelines I found were always missing something so I compiled my own. I present:
The Complete Gyllenswift Timeline
Taylor and Jake meet at a dinner party at Gwyneth Paltrow’s house, “a while ago” Gwyneth said in December 2010 (link)
October 23 Taylor and Jake are spotted apple picking in upstate NY (link)
That same day, Emma Stone hosts SNL and Taylor and Jake show up to the taping together. People reported, “they walked around together backstage, but they were careful not to be seen too close. It was hard to tell if they were together, but everyone was shocked that she brought him.” Sources at SNL told Lainey Gossip: "She was totally into him. They were close the whole time, and awkwardly cute-flirting, some undercover handholding ... It was more than just friends." (link)
October 24 Taylor and Jake are spotted in Brooklyn getting brunch with Emma Stone (link)
October 25 Jake supposedly accompanies Taylor to a taping of an NBC Thanksgiving special and hangs out in her dressing room with Andrea (link)
October 29-November 1 Jake and Taylor have a getaway in Big Sur (link). According to People, "they spent most of their time in their room - the most expensive one in the hotel...they did step out for a romantic dinner at Sierra Mar. They were very cute. They looked happy." They "were seen together over breakfast and also by the pool.”
November 1 Taylor and Jake stop in Santa Barbara for ice cream and take photos with fans (link)
Taylor’s appearance on Ellen airs and Ellen grills her about Jake, asking “Are you optimistic about love?” (video)
November 11 Jake charters a plane, for a reported $150,000-165,000 to fly Taylor to London while he promotes his film Love & Other Drugs (link) He is photographed in London wearing the famous scarf from Thanksgiving.
November 25 Taylor celebrates Thanksgiving with the Gyllenhaal family. She and Jake get maple lattes from a coffee shop in Brooklyn and are papped together (link). She is also photographed with Maggie and her daughter.
They travel to St Louis to spend time with Taylor’s extended family (link)
November 27 Taylor and Jake are spotted having coffee in Nashville (link) and later looking at Christmas decorations at the Gaylord Opryland (link)
November 28 Jake and Taylor have coffee in Nashville (link)
November 29 Taylor and Jake grab coffee in Nashville (link)
November 30 Taylor and Jake get coffee in Nashville (link)
First week of December Jake rents out an entire movie theatre so they can see Tangled in private (link)
December 8 Taylor flies to LA to see Jake (link)
December 9 Jake and Taylor are papped in his car, with Jake looking angry and yelling at the paparazzi. He calls the police on them for reckless driving (link)
December 13 Jake reportedly gifts Taylor a $10,000 Fender Gretsch signed by Chet Atkins (link), a $100,000 bracelet, 21 pounds of coffee, a coffee grinder and coffee maker, and he made her a birthday card (link). But he skips her birthday party. Radar reports in 2014: “The day before — all was set — he was coming, no issues. But the day of, she doesn't hear from him at all. No texts, no calls," the insider revealed. "Taylor thought maybe he was planning some sort of surprise. Nope. He didn't show up and she locked herself in the bathroom and cried the entire night." (link)
January 2011 news breaks of a split. A source tells People “They’re over. It ended last month.” Allegedly Jake broke up with her over the phone right before New Year’s. US Weekly reports “He said he wasn’t feeling it anymore and was uncomfortable with all the attention they got. Taylor is really upset. We told her not to move so fast with this, but she didn’t listen.” “Jake cares about her, but [the publicity] was a lot for him. He wants to keep his private life private, and that’s hard to do dating Taylor. Jake just told her it wasn't working out. Taylor is really upset and hurt. She doesn't know what she did for him to put a stop to it. She feels really burned by him." (link)
January 15 Jake flirts with Camilla Belle at an event (link)
January 16 Jake takes ex girlfriend Jenny Lewis as his date to the Golden Globes (link), they insist they are just friends.
January 19 Jake and Taylor have dinner in Nashville. Us Weekly reports, “He wanted to take her to dinner, but she said she had to rehearse. He said he didn’t think they ended things right, and he owed it to her to talk face to face… he said he just wasn’t feeling things anymore. He didn’t like where things were headed.” (link)
February 27 Taylor and Jake are spotted at the Vanity Fair Oscar Party, "outside near the restroom having a discussion. It seemed a bit more serious – it certainly wasn't a 'Hi, how are you?' talk. It seemed like they were catching up, sorting something out." A Washington Post reporter seated near Gyllenhaal and Swift remarked: "Gyllenhaal is using words like 'care' and 'feel'. It is not a good spot to linger." (link)
August 30 2012 We Are Never Ever Getting Back Together video premieres (video). Taylor sports glasses similar to those worn by Jake and the video briefly depicts Taylor and the video boyfriend fighting in a car. The boyfriend takes his scarf off and wraps her in it.
January 2013 in an interview with a Spanish TV show, Taylor says “I think once a relationship is done it’s done, you can’t do that back and forth thing it’s the most exhausting process.” When asked about important characteristics to look for, she replied, “I think you have to have somebody that’s dependable, that isn’t going to change their mind every five seconds.” (link)
November 2013 Taylor says “I heard from the guy that most of 'Red' is about. He was like, ‘I just listened to the album, and that was a really bittersweet experience for me. It was like going through a photo album.’ That was nice." (link)
May 5 2014 Jake attends the Met Gala, as well as Taylor and other exes Kirsten Dunst and Reese Witherspoon. (link)
January 12 2015 Us Weekly reports that Jake and Taylor have a run in at a Golden Globes after party. “Taylor was also seen on the dance floor, but not dancing. She had a friend with her and supposedly kept telling her friend that “We have to go, we have to go”. They ran off to the bathroom where there was a summit with Cara Delevingne and some others. US’s source says Taylor seemed like she was having a meltdown and had to be comforted by Cara who had her arm around her. Shortly after that, she was seen in the lobby, pacing in circles with smudged eye makeup, looking or waiting for her friends. Later on, she and Cara were on a bench outside talking privately.” (link) OK! Magazine reports he sent her flowers after the awkward encounter (video).
January 13 2015 Lainey Gossip notices that Us Weekly has changed the story (link). Now it is reported “Taylor and her friends arrived at the Chateau Marmont just before 2 a.m. and Jake was there in the lobby. He was leaving as she was coming in. Taylor ran up and gave him a big hug and they caught up. They were smiling and looked like any old friends catching up.”
July 2015 Jake is interviewed on Good Morning America promoting his film Southpaw and Bad Blood plays in the intro (link). A rep for GMA tells Gossip Cop it was a coincidence.
July 2015 Jake appears on Howard Stern, and denies he heard the song playing. When asked if he would recognise a track recorded by Swift, he said “Of course." However, when asked if he is aware there are love songs written about him, he said "Do I? I don't know." Jake also calls Taylor a “beautiful girl.” (link)
November 2015 OK! Magazine reports Jake and Taylor are speaking after Jake asked Cara Delevingne for Tay’s phone number (link). And that “he said he owed Taylor an apology for how things ended between them.” The report continued that Taylor and Jake had been speaking secretly behind Calvin Harris’s back. A source close to Taylor denied saying, “That is complete nonsense of her being in contact with Jake. She is devoted to Calvin and her career which are both going strong. She is not seeking anything from past boyfriends at all. She doesn't talk to Jake.” (link)
September 2017 on Watch What Happens Live, Andy Cohen asks Maggie about the scarf “I never understood why everybody asked me about this scarf. What is this?” “I am in the dark about the scarf. It’s totally possible. I don’t know. I have been asked this before, and I've been like what are you talking about.” When Andy says to look for it, she laughs and says “it’s possible.” (link)
July 2020 Jenny Lewis tweets:
November 2020 In a podcast with Rolling Stone, Taylor called Red a 'pure heartbreak' album, saying: "I look back on this as my only true break up album. Every other album has flickers of different things – this was an album that I wrote specifically about a pure, absolute, to the core heartbreak." (link)
November 5 2021 Taylor announces her short film of All Too Well (10 minute version). The cast includes Sadie Sink, 19, and Dylan O’Brien, 30, the same age difference Jake and Taylor had.
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