- Copiously Credited Creator: Taylor Swift wrote, directed and starred (although not in a large role).
- Creator-Chosen Casting: According to Swift, stars Dylan O'Brien and Sadie Sink were the two actors she had in mind from the earliest of planning stages, and she didn't have backup ideas in case they said no.
- Playing Against Type:
- Sadie Sink was best known for Stranger Things and Fear Street, playing outspoken Plucky Girls, so it was slightly different to play a straight dramatic role in which she's more naive and less Wise Beyond Her Years.
- Dylan O'Brien is better remembered for Teen Wolf and The Maze Runner Series, playing heroic teens. It's surprising not only to see him play his actual age (29) but as the abusive boyfriend.
- Sleeper Hit: Swift has admitted to being surprised at the success of "All Too Well", since it was not one of the singles of the album, didn't get a music video, and wasn't particularly promoted by her team. Regardless, it grew a cult following and is regarded by critics to be one of her best songs. Fast forward to 2021, and the conversation around the release of Red (Taylor's Version) was strongly dominated by the song's ten-minute version, and the video would go on to win Video of the Year at the MTV Video Music Awards. Michael Bublé even homaged the love scene in one of his music videos the next year.
- Throw It In!: The argument in the kitchen was entirely improvised and planned to be part of the montage, but Swift found the material so good it was included in between verses.
- Underage Casting: Sadie Sink only turned nineteen in 2021, and her character turns twenty-one in the short.
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