Before their collaboration in the short film adaptation of "All Too Well" in 2021, Dylan O'Brien was a fan of Swift's music. After Swift announced the release of "Evermore" in December 2020, the "Teen Wolf" star tweeted a "thank you" gif in response, and later revealed in a 2021 interview with Coup de Main that he personally loves the songs, "Mirrorball," "My Tears Ricochet," "Mad Woman," "Epiphany," and "The 1."
In November 2021, O'Brien starred alongside "The Whale" actor Sadie Sink in Swift's short film version of "All Too Well." Reflecting on O'Brien's performance, Swift told Bustle via email in March 2022, "I had a feeling he would be great at ad libbing and adding nuance to his character, which enriched the story tenfold...He absolutely blew me away and I feel really lucky that I gained such a great friend from the experience too."