Jake Gyllenhaal Once Reportedly Spent $165,000 on a Date with Taylor Swift

Who

Oscar-nominated actor Jake Gyllenhaal, 41, and 11-time Grammy-winning musician Taylor Swift, 32.

How They Met

Though Swift and Gyllenhaal were first spotted together backstage at a taping of Saturday Night Live in October 2010, their history goes back before that, when they were set up by a mutual friend — Gwyneth Paltrow.

In a December 2010 interview, Paltrow reluctantly admitted to having played matchmaker after a report surfaced indicating that Swift and Gyllenhaal met at a dinner party at the London home Paltrow shared with then-husband Chris Martin.

"I've just known Jake for a long time and he's a great guy," she said at the time. "And Chris has a friendship with Taylor." Though the only timeline Paltrow gave for the dinner party was "a while ago," it was clear by October of that year that something was brewing between Swift and Gyllenhaal. A source told People they had shown up to the SNL taping together, and that "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."

Why We Loved Them

The weekend of the SNL spotting, Gyllen-Swift (Swift-Haal?) were also seen having brunch in Brooklyn. This kicked off a season of autumnal dates that culminated in one of the few public photographs of the two of them together, taking a stroll in N.Y.C. in the ultimate 2010s fall outfits: an ultralight down puffer jacket for him and a short coat with Oxford shoes for her.

Given that the relationship lasted as long as the fall season, the Gyllen-Swift fall agenda was in full force, with appropriately-themed maple latte coffee dates (multiple) on deck. Throw in Swift's reference to "autumn leaves falling" in a song purportedly written about Gyllenhaal (more on that later), and now, when we think of fall, we think of them. It may have been a brief affair, but for a fleeting moment, Swift and Gyllenhaal encapsulated the cuffing season aesthetic, and for that, we loved them.

When They Peaked

Never let it be said that Jake Gyllenhaal doesn't know how to do grand gestures. Apparently, the actor once shelled out a reported $165,000 to fly Swift to London, where he was promoting his movie Love and Other Drugs, just so they could spend 24 hours together. If that isn't a romantic date, we don't know what is. Perhaps the time he rented out a whole movie theater so they could see Tangled together in privacy?

The Breakup

By the new year, the autumnal coffee dates and strolls were officially done, after the pair reportedly spent the holiday apart. Swift rang in 2011 solo in Nashville, while Gyllenhaal was in New York City, where he attended a closing party for Broadway's Fela! on January 2. A source confirmed the breakup to People in early January with an aptly succinct quote, telling the outlet, "They're over. It ended last month."

As the magazine noted at the time, no reason was given for the breakup, though the relationship (and, presumably, the split) appeared to provide fodder for one of Swift's most iconic hits. It's now widely accepted that "All Too Well" off Swift's Red album was penned about her relationship with Gyllenhaal, with all of its references to the subject having once been "a little kid with glasses" and a scarf left at his sister's house (hi, Maggie Gyllenhaal).

The rumor that the song is about Gyllenhaal has been so widespread that Maggie G. has been forced to publicly answer for the scarf's whereabouts, though she's insisted, "I am in the dark about this scarf. It's totally possible [it's at my house]. I don't know. I have been asked this before, and I am like, 'What are you talking about?'"

Jake, meanwhile, has never been able to shake the association with the song. Swifties flooded his Instagram with red scarf emojis after he shared a photo of himself as, you guessed it, "a little kid with glasses."

Not that he'll talk about it, of course. When asked by a Guardian reporter in 2017 if he thought dating Taylor Swift was "playing with fire" for someone so intensely private, the actor said, "I think when you're in a relationship, you are constantly scrutinized, your friends are scrutinized, but ..." before trailing off.

"I would love to not talk about my personal life," he concluded. Fair enough.

Where They Are Now

Swift went on to be romantically linked to Conor Kennedy, Harry Styles, Calvin Harris, and Tom Hiddleston, before meeting her current partner, Joe Alwyn. Though she and Alwyn are notoriously private about their relationship, she thanked Alwyn during her Album of the Year Grammy acceptance speech in March 2020.

"Joe, who is the first person that I play every single song that I write, and I had the best time writing songs with you in quarantine," Swift said.

Gyllenhaal, meanwhile was linked to actresses Jessica Lowndes and Minka Kelly, as well as model Alyssa Miller. Since 2018, he's been rumored to be dating model Jeanne Cadieu.

#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.