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Dylan O'Brien Will Star In A Short Film About Taylor Swift's Most Heartbreaking Song

Dylan O'Brien in Love and Monsters and Taylor Swift in ME! music video
(Image credit: Paramount/Universal Music Group)

Taylor Swift is currently going down memory lane as she steadily re-records and releases each of her first six albums following her master recordings being sold off by Scooter Braun. The Grammy-winning singer started with her second album Fearless early this year and next in line fans will revisit her fourth album, Red, which was originally released in 2012. In anticipation for its re-release this Friday, Swift has announced she’ll also be sharing a short film starring the likes of Maze Runner star Dylan O’Brien. 

Taylor’s Version of Red will be a 30 song album featuring re-records of big hits like “I Knew You Were Trouble,” “22” and “We Are Never Ever Getting Back Together,” but many Swifties are especially excited for “All Too Well.” The song is arguably Swift’s most heartbreaking song of all time and many of her fans’ favorite of hers. It’s already been announced that there will be a ten-minute version of “All Too Well” to close out the record, but now we’ve learned a short film will come out as well. 

Swift surprised fans when she posted a short teaser of an “All Too Well” short film that has been written and directed by herself and will feature the acting talents of Dylan O’Brien along with Stranger Things’ star Sadie Sink. The Instagram post features a winding road decorated with autumn trees and a vintage car going down the road. It’s the perfect reference to the lyric “autumn leaves falling down like pieces into place / And I can picture it after all these days.” 

It’s an interesting project for Maze Runner’s Dylan O’Brien to take on in between wrapping the action franchise and rocking bleach blonde hair for a new movie called Not Okay. Sadie Sink memorably joined Season 2 of Stranger Things to play Max Mayfield and also recently starred in Netflix’s recent Fear Street movies

“All Too Well” is a beautiful song that has Taylor Swift reminiscing on a relationship after it has ended and all she has left of it is her memories to keep her warm. It is rumored to be about a relationship she had with actor Jake Gyllenhaal. It’s possible Dylan O’Brien will play the love interest to Taylor Swift in the short film, but we’ve also come to expect the unexpected from the artist. There could be a completely different angle here. 

What’s interesting is Sadie Sink is currently 19 and Dylan O’Brien is 30 years old, which is quite similar to the ages of Swift and Gyllenhaal at the time they were dating. Swift was 20 and Gyllenhaal was 29. Perhaps it will feature Taylor Swift looking back on a fictionalized version of the relationship like theirs almost a decade later? We’ll find out on Friday, November 12 when the “All Too Well” short film comes out! 

Sarah El-Mahmoud

YA genre tribute. Horror May Queen. Word webslinger. All her writing should be read in Sarah Connor’s Terminator 2 voice over.