Inside Taylor Swift's Friendship With Dylan O'Brien

Dylan O'Brien and Taylor Swift's friendship may have only found its way into the public eye in 2021, but they've been fans of each other for much longer. In 2014, the pop titan took to X, formerly known as Twitter, to share her rollercoaster experience watching O'Brien's "The Maze Runner." The film's cast later did an MTV interview where they tried to guess O'Brien's go-to karaoke song (via YouTube). Jacob Lofland wrote "Shake It Off" as his guess and shared that he had witnessed his co-star sing his heart out to the catchy track. Thomas Brodie-Sangster had the same idea, and his fellow actors, Ki Hong Lee and Dexter Darden agreed it would be a top pick for O'Brien. 

In another clip shared on YouTube, a fan asked the cast who would play if their character's gender was different. James Dashner, the author of "The Maze Runner" series answered that he had always thought of O'Brien's character as Swift. The lead actor seemed pleased with the answer and complimented the "Blank Space" singer's good looks. 

O'Brien got more vocal about his love for Swift in 2020. After she announced her ninth album, "Evermore," he quoted her post on X and used a gif of Dwight Schrute saying "thank you" to express his excitement. When she released her politically-charged track "Only The Young," O'Brien appreciated the track in a tweet "This is why we stan." After Smash Mouth called her album "Folklore" "Borelore" on X, O'Brien defended it by simply writing, "F*** Smash Mouth."

Taylor Swift's "Folklore" seems to hold a special place in Dylan O'Brien's heart. Speaking to Coup de Main in April 2021, the "Teen Wolf" alum gushed about Swift's work ethic through the pandemic which enabled her to drop two new albums. He also named a few favorites off "Folklore" and noted that "Mirrorball" was an underrated bop. Later in the year, Swift revealed that she had directed and written "All Too Well: The Short Film" and cast O'Brien and Sadie Sink in the lead roles. 

In a 2022 Bustle interview, Swift gushed, "Dylan was my first choice for the 'All Too Well' short film because he has that versatility I was looking for," she continued. "I'd seen his work and heard nothing but wonderful things about him as a person." She later added that she had a hunch that he could bring more depth to her words with a nuanced performance. As a result, the "Lover" songstress wrote him a lengthy text to get him on board, but he agreed to join in a heartbeat. 

O'Brien shared that Swift was a phenomenal director because she had a well-thought-out vision for the film but was happy to incorporate his and Sink's ideas. While speaking at the Tribeca Film Festival, "The Outfit" actor recalled that during their first meet, the pop sensation told him that she wanted his character to be charming despite all his shortcomings. He added that the conversation led him to understand how Swift's empathy gave her a unique perception of people. 

When Dylan O'Brien spoke to Extra TV, the interviewer asked if "All Too Well" was about Taylor Swift and Jake Gyllenhaal's relationship. O'Brien protected his friend's privacy by saying he was playing a character called Brandon and didn't know much else. In an Entertainment Tonight interview, O'Brien shared that he stayed in touch with Sadie Sink and Swift through a group chat, and revealed that she shared the news of "All Too Well: The Short Film's" VMA nominations soon after she found out. 

O'Brien joined her for the ceremony, and the duo seemed to be having a blast as they danced to the performances. He hugged Swift as their work bagged the Video of the Year award and applauded her as she announced her 10th album, "Midnights" in her acceptance speech. However, his contributions to the record-breaking album didn't end there, because he was credited for drums on "Snow On The Beach."

 While appearing on "The Tonight Show With Jimmy Fallon" Swift shared that O'Brien, who is a drummer, was present at Jack Antonoff's studio while they were recording the track. She added that everyone got a little tipsy and the actor got on the drums to mess about, but then they officially asked him to play the track on the drums. O'Brien is also credited with 'crowd applause' for "Question ... ?" and Swift later shared a video of him recording his part alongside Antonoff's sister, Rachel Antonoff, and her brother, Austin Swift (via YouTube).