While some of us remember Jake Gyllenhaal‘s dating history ~all too well~, others need a reminder! The Brokeback Mountain actor has dated several A-list women during his time in the spotlight, including Kirsten Dunst, Taylor Swift and more.

As of 2021, Jake is in a relationship with girlfriend Jeanne Cadieu. However, it’s his previous romance with Taylor that continues to make headlines. The Academy Award nominee and the “Tolerate It” artist dated from around October 2010 to January 2011.

Taylor immortalized their three-month relationship in a song titled “All Too Well” off her 2012 album Red. Later, in November 2021, the eleven-time Grammy Award winner released Red (Taylor’s Version), as well as a new 10-minute version of “All Too Well.”

Jake is mortified that Taylor has targeted him in ‘All Too Well,’” a source exclusively revealed to Life & Style after the 10-minute version’s release. “He’s such a private person and goes out of his way to avoid drama, so having their three-month fling dragged up in the song and hearing people gossip about it is a hard pill for him to swallow.”

According to the insider, Jake “thought” Taylor “was over” their relationship. “It seems like anyone who has dated her can’t escape from their past.”

After the album’s initial release, Taylor claimed Jake didn’t take issue with any of the music. “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,” the West Reading, Pennsylvania, native, who has since moved on with boyfriend Joe Alwyn, told New York magazine in 2013.

“Nicer than, like, the ranting, crazy e-mails I got from this one dude. It’s a lot more mature way of looking at a love that was wonderful until it was terrible, and both people got hurt from it — but one of those people happened to be a songwriter,” Taylor added. “So, what are you going to do? Did you not Wikipedia me before you called me up [for a date]?”

Scroll through the gallery below to learn more about Jake Gyllenhaal’s complete dating history.


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Tyler Cowan