Jake Gyllenhaal Can't Escape Any Taylor Swift Drama on 'SNL' Because of This Musical Connection

The May 18 episode of Saturday Night Live is going to be slightly unhinged because Jake Gyllenhaal is hosting the show while a very close friend of Taylor Swift’s is the musical guest. There is no way the show’s writers can avoid the very obvious connection, so the big question is: How will they address Gyllenhaal’s former relationship with the “Shake It Off” singer and Sabrina Carpenter’s participation in the Eras Tour as the opening act?

Gyllenhaal knows “All Too Well” what it’s like to draw the ire of Swifties because that song from the Red and Red (Taylor’s Version) album is reportedly about their short-lived romance. The Roadhouse actor has probably heard more about Swift’s scarf that was left at his sister Maggie Gyllenhaal’s house than her ever wanted to. Where is that red scarf, Jake? The couple dated briefly in 2010, but ever since her first version of Red came out in 2012, his life has never been the same. 

He probably cringed when he heard that Swift was rerecording the album after a very big feud with Scooter Braun, but Gyllenhaal has kept it classy in the press. “Artists tap into personal experiences for inspiration, and I don’t begrudge anyone that,” he said diplomatically to Esquire in 2022. Maybe SNL writers will be smart enough to have him come out in a red scarf during his monologue? While viewers have to wait two weeks to find out how this Swift connection plays out, fans are already weighing in on X to share their thoughts. 

“snl knew what they were doing pairing jake gyllenhaal and sabrina carpenter together.. they messy as hell for that. whoever paired them together deserves a raise,” wrote one social media user. “Sabrina Carpenter is gonna cover All Too Well on SNL while Jake Gyllenhaal grimaces in the background and it’s gonna turn this place into a crime scene for 48 hours,” joked another account. We also love the smart fans who are thinking about the comedic possibilities with this awkward pairing. “Sabrina being the musical guest while Jake Gyllenhaal is the host… I need the SNL writers to get working on an All Too Well skit for both of them IMMEDIATELY,” a Swiftie wrote.

However this plays out, we have a feeling Swift will be tuning in because she’s supportive of the women in her orbit, and she’s going to root for Carpenter. We have no idea if she will be cheering on Gyllenhaal though. 

Before you go, click here to see celebrity exes who never buried the hatchet.