Taylor sent Dylan a novella-length text message asking him to appear in the short film and he agreed without hesitation. She told Bustle in 2022: “Dylan was my first choice for the ‘All Too Well’ short film because he has that versatility I was looking for. 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. 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.”
Taylor has stated that All Too Well (The Short Film) was shot on 35 mm film by Japanese-Korean-British cinematographer Rina Yang. Yang used an Arri Arriflex 235 for handheld and steadicam, and Panavision MXL for dolly work; lenses were Panavision Primo, with 11:1 Primo zoom. She shot exterior scenes on Kodak Ektachrome—the same kind she had used to shoot the HBO television series Euphoria. Taylor cited “Barbara Stanwyck films, particularly 1937’s Stella Dallas,” John Cassavetes, and Noah Baumbach, especially his Marriage Story (2019), as artistic influences for the short film.
On November 5, 2021, Good Morning America revealed a teaser for a short film written and directed by Taylor, titled All Too Well (The Short Film), based on the song. The teaser showed a vintage car driving down on a road surrounded by autumnal trees, and its cast consisting of Taylor, American actress Sadie Sink, and American actor Dylan O’Brien.
The film’s world premiere took place on November 12 at the AMC Theatres in Lincoln Square, New York City with an audience that included Taylor, Sink, O’Brien, journalists, film and music critics, and handpicked fans.Each audience member received an autographed movie poster and a custom packet of tissues.Taylor also performed “All Too Well (10 Minute Version)” in the theatre after the screening. The film was later released on the same day on YouTube. It had a limited theatrical release in major cities.
On June 11, 2022, the short film had a special screening at the 2022 Tribeca Film Festival at the Beacon Theatre in New York City. In an interview with American director Mike Mills, Taylor discussed her filmmaking process, while Sink and O’Brien talked about their characters in the film. Paula Weinstein, the chief content officer of the festival, said in a statement regarding Taylor: “We are very excited and enthusiastic to present a compelling slate of Reunions, Master Classes and Talks from one of the most leading and well-known storytellers from all across art, comedy, music, television and film.”
The film was screened in its 35 mm form for the first time at the 2022 Toronto International Film Festival on September 9, 2022, at the TIFF Bell Lightbox in Toronto, Ontario; Taylor was interviewed by the festival’s CEO, Cameron Bailey, regarding “[her] filmmaking and visual aspects of her music.”
Taylor took part in the Variety “Directors on Directors” series opposite British-Irish filmmaker Martin McDonagh in December 2022. Ramin Setoodeh, co-editor-in-chief of the publication, stated, “Since Taylor Swift premiered her short film All Too Well last winter in New York, Variety has been impressed with her vision as a director.” A video of behind the scenes from the short film was also released on December 8.
The story starts with the couple lying in bed together, Her mesmerized by Him. They travel to upstate New York, where she leaves her red scarf at a house belonging to his sister. Their relationship takes a turn at a dinner party, where Him ignores his girlfriend as he is busy catching up with his friends. They fight afterwards; Him is arrogant and dismissive, while a distraught Her is heartbroken but still wants to stay with Him. He apologizes and kisses her to end the argument, and they dance in the refrigerator light. Eventually, Him starts to not be there for Her when she needs him, leading to Him breaking up with Her. A devastated Her weeps in bed, ignoring his phone calls. A montage shows Her alone at parties and miserable on her 21st birthday. At the movie’s premiere, Taylor said:
Him’s life carries on as he walks alone down a Brooklyn street, recalling some of the happier moments in his relationship with Her. The film then jumps 13 years into the future. Her has become an author (now portrayed by Taylor) and is celebrating the release of her novel All Too Well, presumably detailing the heartache of her early twenties, by reading it out to an audience of fans in a packed bookstore. Outside, an older Him watches Her through the window, wearing the same scarf she had abandoned years earlier.
All Too Well (The Short Film) was met with critical acclaim. Brittany Spanos of Rolling Stone called it a “dramatic and moving” film that “digs deep into heartache and scarf lore”. Rhian Daly of NME said the film underscores “the emotional power of [Taylor’s] storytelling” with “devastating” cinematography and “electric performances” by Sink and O’Brien. In Collider, Shane Romanchick wrote the film “recontextualizes how relationships, through all their painful and rose-colored moments, help us grow to be better people”. Karl Quinn, in his review for The Sydney Morning Herald, complimented the “gorgeously cliched Notebook-style” screenplay, Taylor’s direction, and the “finely tuned” performances of Sink and O’Brien. Film critic Steve Pulaski said All Too Well (The Short Film) is “a bold, brilliant work that illustrates the ongoing maturation of Swift as more than a singer-songwriter” and dubbed her “an impeccably gifted storyteller with her detail-oriented narratives”. He also praised Rina Yang’s “gorgeous autumnal” cinematography.
Indie Shorts Mag, rating the film 4.9 out of 5, praised the direction and dubbed the film “apotheosis of Taylor Swift’s discography, lore and fandom”. Critics At Large critic CJ Sheu lauded Taylor’s craftsmanship, Yang’s cinematography, and Sink’s “engrossing” performance. He called the dialogued argument a “powerful scene”. In USA Today, Patrick Ryan wrote that the film was “operatic in its emotions and scope” and felt the argument scene was “particularly gut-wrenching”. Billboard‘s Paul Grein also praised the argument, saying the writing in the scene is “so vivid that it’s easy to see Swift winning an Oscar for screenwriting one day”.
All Too Well (The Short Film) has received awards recognition in a diverse set of fields. It received five nominations at the 2022 MTV Video Music Awards, winning “Video of the Year,” “Best Longform Video,” and “Best Direction”; Taylor became the first act in VMA history to win “Video of the Year” three times. It also won “Best Video” at the 2022 MTV Europe Music Awards. The film won the awards for “Favorite Music Video” and “Best Music Video” at the 2022 American Music Awards and 65th Annual Grammy Awards (2023), respectively. Taylor reacted to her win at the Grammys by writing:
Publications have described the short film as one of the biggest newsmakers and pop culture moments of 2021. Canadian singer Michael Bublé, in the music video for his 2022 single “I’ll Never Not Love You,” referenced and recreated iconic “love scenes” from various movies with his wife, Luisana Lopilato; it included All Too Well (The Short Film), with Bublé as Him and Lopilato as Her. The Department of English of the Queen’s University at Kingston, a public research university in Ontario, Canada, offers a fall semester course titled “Taylor Swift’s Literary Legacy (Taylor’s Version)”, with a syllabus requiring students to analyse many of Taylor’s works, such as All Too Well (The Short Film), to understand their literary references and sociopolitical relevance in contemporary culture.