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Taylor Swift’s Music Video Boyfriends: Where Are They Now

Taylor Swift’s Music Video Boyfriends: Where Are They Now

Dylan O’Brien From “All Too Well”

As fans know all too well, Dylan O’Brien starred opposite Sadie Sink for the 2021 short film long rumored to be about Taylor’s relationship with ex Jake Gyllenhaal.

“Dylan was my first choice for the ‘All Too Well’ short film because he has that versatility I was looking for,” the singer wrote in an email to Bustle in 2022. “I’d seen his work and heard nothing but wonderful things about him as a person. Ultimately I want to work with people who love what they do and come at it with enthusiasm, because that’s how I approach creating things too.” 

After Taylor sent a long text asking Dylan to take the part, he agreed.

“I had a feeling he would be great at ad libbing and adding nuance to his character, which enriched the story tenfold,” she added. “He absolutely blew me away and I feel really lucky that I gained such a great friend from the experience too.”

The Maze Runner actor can still picture it after all these days.

“It was an immediate yes,” he told Extra at the premiere. “I couldn’t believe that she called me for this. I couldn’t believe she knew who I was. It was hilarious. We were cracking up about that.”

Since then, Dylan has appeared in several more films, including The Outfit, Maximum Truth, Ponyboi, Caddo Lake and Twinless.


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