Taylor Swift and Jake Gyllenhaal's Relationship: A Look Back

Taylor Swift and Jake Gyllenhaal's brief romance may have taken place over a decade ago, but the singer's fans still remember it "All Too Well."

The Grammy winner and the Donnie Darko star first made headlines in 2010, when they were spotted together in New York City. Over the next few months, the pair's romance heated up and they were famously photographed walking arm-in-arm on Thanksgiving together.

By the end of the year, things had gone south for the new couple: their split was confirmed after they spent their December birthdays and the holidays apart.

While neither Swift nor Gyllenhaal have spoken publicly about their relationship, Swift's fans have long believed that a number of her songs on Red, including her epic heartbreak ballad "All Too Well," were inspired by Gyllenhaal.

When the popstar re-released a 10-minute extended version of the song in November 2021, Swifties quickly dissected the lyrics for potential clues leading back to Gyllenhaal — and they weren't disappointed.

After releasing her tenth studio album Midnights, Swift had fans theorizing that breakup song "Maroon" — "a darker & more mature shade of RED," noted one — was a follow-up to Red. (Other eagle-eyed Swifties pointed out Swift wore her Red ring in a TikTok revealing the title of the song.)

Though the former pair have both long since moved on — Swift has been dating British actor Joe Alwyn since late 2016, while Gyllenhaal has been dating model Jeanne Cadieu since 2018 — fans haven't quite let it go.

From their first date to their split and the ways they've seemingly acknowledged each other since, here's everything to know about Taylor Swift and Jake Gyllenhaal's previous relationship.

October 23, 2010: Taylor Swift and Jake Gyllenhaal are spotted backstage at Saturday Night Live together

The pair first sparked romance rumors when they were seen backstage together at Saturday Night Live, which was hosted by Swift's close friend Emma Stone.

"They showed up together," a source told PEOPLE at the time. "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."

October 24, 2010: Taylor Swift and Jake Gyllenhaal grab brunch in Brooklyn

The next morning, the pair were spotted getting brunch with 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.

November 25, 2010: Taylor Swift and Jake Gyllenhaal spend Thanksgiving together

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 Gyllenhaal lived nearby, and the pair were famously photographed holding hands while out and about with her and her children that day.

November 27, 2010: Taylor Swift and Jake Gyllenhaal visit Nashville together

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."

November 28-30, 2010: Taylor Swift and Jake Gyllenhaal continue their coffee tour of Nashville

Swift and Gyllenhaal's romance appeared to be a highly-caffeinated one, as the duo were spotted at two more coffee shops during their long-weekend Nashville getaway. First, they were seen getting their java fix at the Frothy Monkey, before popping into another local spot called Crema the next day and then returning the following morning to the Frothy Monkey again, where the actor allegedly ordered a cappuccino with maple syrup.

December 9, 2010: Taylor Swift and Jake Gyllenhaal spend time together in Los Angeles

After a week apart, the Grammy winner and the actor were reunited in Los Angeles. As soon as she landed, the singer made her way to Gyllenhaal's Hollywood Hills home, PEOPLE reported.

December 10, 2010: Taylor Swift and Jake Gyllenhaal drive around Los Angeles

​​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."

December 13, 2010: Taylor Swift turns 21 and celebrates without Jake Gyllenhaal

The singer threw herself a Christmas-themed birthday party at 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 dad with self-effacing jokes / Sipping coffee like you're on a late-night show / But then he watched me watch the front door all night, willing you to come / And he said, 'It's supposed to be fun turning twenty-one.' "

Gyllenhaal turned 30 a few days later, on December 19 — sans Swift.

January 4, 2011: Taylor Swift and Jake Gyllenhaal split

"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.

January 19, 2011: Taylor Swift and Jake Gyllenhaal spark reconciliation rumors in Nashville

A few weeks after their split, the former couple briefly reunited, sparking rumors that they'd gotten back together. They were seen arriving together at Bound'ry, a restaurant near Swift's home in Nashville.

"They did eat," a patron told PEOPLE. "They were cordial to one another, but not affectionate."

Another source added that they seemed friendly. "There was no holding hands, but they seemed happy together," the source said. "They sat next to the fireplace just chatting away."

February 27, 2011: Taylor Swift and Jake Gyllenhaal run into each other at an Oscars afterparty

Swift and Gyllenhaal saw each other once again the following month at an Oscars afterparty.

"It seemed like they were catching up," a source told PEOPLE of the run-in.

October 22, 2012: Taylor Swift releases Red

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 Swift legend: "And I left my scarf there at your sister's house/ And you've still got it in your drawer even now."

The pair had previously been spotted wearing the same scarf in November 2010, prompting fans to believe this was a direct reference to the Thanksgiving she spent with the actor and his sister, Maggie.

Another lyric also seems to point to Gyllenhaal: "We were singing in the car getting lost upstate." The actor's penchant for singing is well-documented, and the pair allegedly were spotted apple-picking together upstate during their brief courtship.

January 11, 2015: Taylor Swift and Jake Gyllenhaal catch up after the Golden Globes

Four years after their split, the "Mean" singer and the Southpaw star bumped into each other as they arrived at a Golden Globes afterparty at Chateau Marmont in Los Angeles.

Just before heading into the fête, Swift and Gyllenhaal briefly chatted in the lobby of the hotel, where the singer introduced her former beau to her friends, including her close pals, the Haim sisters.

July 22, 2015: Jake Gyllenhaal calls Taylor Swift a "beautiful girl"

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 suggested that perhaps the actor had a song written about him. "Do I?" Jake replied. "I don't know."

During the interview, he also admitted that he'd only been in love "twice" before, adding that he was responsible for his past relationships ending. "It was me, man. I think I probably just got scared."

September 13, 2017: Maggie Gyllenhaal says "it's totally possible" that Swift may have left a scarf at her home

Jake's older sister Maggie Gyllenhaal chimed in on the whereabouts of the famous scarf during a visit to Watch What Happens Live.

"I never understood why everybody asked me about this scarf," the actress and director said when asked by host Andy Cohen about the rumors that Swift had left her scarf at her house. "What is this?"

Cohen then shared Swift's lyric from "All Too Well," "Left my scarf there at your sister's house."

"I am in the dark about the scarf," Maggie responded, before adding: "It's totally possible. I don't know. I have been asked this before."

September 19, 2017: Jake Gyllenhaal smoothly evades questions about Taylor Swift

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 Swift would write a song about it?" Bauman, who lost his legs in the attack, asked Gyllenhaal. "Like a country song?"

"For me, or about it?" Gyllenhaal replied.

"For you," Bauman said. "Like a country song."

"She sort of moved more into pop now," Gyllenhaal said, sparking headlines that he had "finally" answered questions about Swift.

November 17, 2020: Taylor Swift says she was "a broken human" when she wrote "All Too Well"

Swift later opened up to Rolling Stone's 500 Greatest Albums podcast about the experience of writing "All Too Well," explaining that the song was written while she was in a dark place.

"It was a day when I was just, like, a broken human, walking into rehearsal just feeling terrible about what was going on in my personal life," Taylor told the outlet.

"I just ended up playing four chords over and over again, and the band started kicking in," she said, adding that she "just started singing and riffing and ad-libbing this song." "People just started playing along with me ... I think they could tell I was really going through it."

November 12, 2021: Taylor Swift re-releases Red (Taylor's Version) and the extended version of "All Too Well"

Swift released the highly-anticipated 10-minute version of "All Too Well" along with her Red re-release, and the additional lyrics further fueled fans' belief that the track is about Gyllenhaal.

One lyric in particular stood out, with Swift claiming that the ex in her song blamed their split on their age difference (Gyllenhaal is nine years her senior). She sings: "You said if we had been closer in age / Maybe it would have been fine / And that made me want to die."

She later adds: "And I was never good at telling jokes / But the punchline goes / 'I'll get older, but your lovers stay my age.'"

February 17, 2022: Jake Gyllenhaal breaks his silence on his thoughts about "All Too Well"

For the first time, Gyllenhaal addressed the fan theories that "All Too Well" is about him in an Esquire profile, revealing he hasn't listened to the song.

"It has nothing to do with me," he said. "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 did speak up on being harassed online by fans, saying that he is interested in the "deeper philosophical question" of whether artists can or should "take responsibility for what we put into the world."

"At some point, I think it's important when supporters get unruly that we feel a responsibility to have them be civil and not allow for cyberbullying in one's name," added Gyllenhaal.

October 21, 2022: Taylor Swift releases Midnights, fans speculate if "Maroon" is about Jake Gyllenhaal

Swift released her tenth studio album Midnights, a moody indie-pop concept album inspired by 13 restless nights. As usual, Swift's fans immediately began poring over the album's lyrics to glean any insights about each track's inspiration.

While several songs on the album seem to allude to the singer's long-term relationship with Alwyn, there is at least one track that fans think is inspired by her past love life. The second song on the album, "Maroon," seemingly nods to Swift's Red album, with the songwriter musing on all of the ways the darker version of the color symbolized the demise of her love affair.

While there's no telling exactly what the track is about, fans quickly took to social media to link the lyrics to Swift and Gyllenhaal's previous relationship.