The song title references the "cruel summer" of 2016 when Taylor Swift faced extreme public criticism following her feud with Kanye West and Kim Kardashian over the rapper's "Famous" lyrics, and a beef with Calvin Harris following the end of their relationship. It is the same name as the compilation album West's record label G.O.O.D. Music released in 2012. That difficult time in Swift's life coincided with the start of her relationship with the British actor Joe Alwyn. Whilst Swift was struggling to maintain her composure as West, Kardashian and Harris' attacked her character, she was also falling in love with a "bad boy." Fever dream high in the quiet of the night You know that I caught it Bad, bad boy, shiny toy with a price You know that I bought it Alwyn would soon be her "lover," and much of her Lover album is devoted to her English beau.

Swift referenced her fall out with Kanye West more fully on the Reputation track "This Is Why We Can't Have Nice Things."

Swift teased the song title in the music video for "You Need To Calm Down" during a scene when Adam Lambert tattooed "Cruel Summer" on Ellen DeGeneres' forearm.