How Dylan O’Brien landed his role in Taylor Swift’s All Too Well video

At the 2022 MTV Video Music Awards, Taylor Swift won Video of the Year — among a host of other awards — for the short film “All Too Well (10 Minute Version) (Taylor’s Version)” (via MTV). It’s safe to say that the sad power ballad has become a rallying cry for fans and is Swift’s hit of the moment.

The short follows the story of a girl (Sadie Sink) who enters a relationship with an older man (Dylan O’Brien) and struggles while making many decisions. It doesn’t end well — if they’d been “closer in age, maybe it would have been okay” — but the girl moves on to turn her heartbreak into a bestseller. It seems like a case of life mimicking art, considering Swift now has an award-winning short under his belt.

It’s a big and widely accepted theory that the man the song is about – and the man on which O’Brien’s character is based – is Jake Gyllenhaal. While Gyllenhaal said in a February 2022 meeting with Esquire that “All Too Well (Taylor’s Version)” had “nothing to do with him,” there are entire novels online about why it’s all about the actor. Per Cosmopolitan, Swift’s fans noted that the age difference between O’Brien and Sink is pretty close to the age difference between Gyllenhaal and Swift when they were dating in late 2010, but that’s not why Swift cast O’Brien in the Role of a manipulative older friend.

Dylan O’Brien was Taylor Swift’s ‘first choice’

For a March 2022 feature on Dylan O’Brien for Bustle, Taylor Swift shared that there wasn’t another actor she’d seriously considered for the male lead. “Dylan was my first choice for the short ‘All Too Well’ because it has the versatility I was looking for,” Swift told Bustle via email.

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She added: “I’ve 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 are passionate about it, because that’s how I approach creating things.”

And according to Swift, who is a “huge fan” of O’Brien, the atmosphere on set was great, proving both actors were destined for the roles. “It was really wonderful working with Sadie Sink and Dylan O’Brien. They’re just absolutely — I’m just blown away by what they did in this short,” Swift revealed on Late Night With Seth Meyers. She continued, “The only two people I envisioned playing the two characters were Sadie and Dylan. … If Sadie had said no, I don’t think I would have made it.”

Taylor Swift found a “great friend” in Dylan O’Brien.

Dylan O’Brien is perhaps best known for playing Stiles Stilinksi in Teen Wolf and Thomas in the Maze Runner trilogy. In 2022, he appeared as Colin in Not Okay, starring Zoey Deutch. While most of O’Brien’s roles weren’t gaslighter attractive ones (although Colin definitely has the reach), Taylor Swift had a clear vision of O’Brien as that guy for All Too Well: The Short Film.

“I had a feeling he would be great at promoting and adding nuance to his character, which enhanced the story tenfold,” Swift told Bustle via email. “He absolutely blew my mind and I’m really fortunate that I also made such a great friend through the experience.” Bustle reported that the shoot took two days, and it featured Sadie Sink and O’Brien as their characters and took lots of shots at what fans saw in the final product. Perhaps the most notable example of this is the kitchen argument, the only part that deviates from the lyrics of the song.

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“Everything was planned to be music. But then when we played that scene [with dialogue]. [Taylor] immediately marched over and just said, ‘That’s it. I’m going to play that in the video,'” O’Brien said in the same Bustle interview. “The confidence to just recognize that on set in the moment and absorb what we brought to it [shows how] She’s so healthy with relationships and her instincts.”