Songfacts®:

• This home-for-the-holidays ballad centers on the hometown reunion of two old flames. The female, Dorothea, left her Tupelo hometown to seek stardom in LA, leaving her boyfriend at the time behind. Now she's returned to stay with their parents for a holiday weekend and is considering a romantic rendezvous with her former high school lover.
  
  And the heart I know I'm breakin' is my own
  To leave the warmest bed I've ever known
  We could call it even
  Even though I'm leaving
  And I'll be yours for the weekend
  
  Dorothea knows well that their hookup will only last for a weekend, and it will break her heart again when she returns home.
• The song title implies that the ex-high school lovers' reunion takes place during the festive time of year. It's another of Taylor Swift's canon of holiday songs along with "Christmases When You Were Mine," "Christmas Must Be Something More," "Christmas Tree Farm," and "New Year's Day."
• The song mirrors another Evermore track entitled "Dorothea." That one is sung from the male character's perspective as he reminisces on his high school romance with Dorothea before she left town to achieve stardom in LA.
• The mirrored songs revive Folklore's summer love triangle, which Swift sang of in "Cardigan" (from Betty's point of view), "Betty" (from James' perspective) and "August" (from the unnamed third person's viewpoint). Swift told her fans, "There's not a direct continuation of the Betty/James/August storyline, but in my mind, Dorothea went to the same school as Betty, James, and Inez."
• Swift described this as being about "Dorothea, the girl who left her small town to chase down Hollywood dreams - and what happens when she comes back for the holidays and rediscovers an old flame."
• Swift wrote "'Tis the Damn Season" the night following the first day of rehearsal for the Disney + documentary Folklore: The Long Pond Studio Sessions. Producer Aaron Dessner recalled to Billboard they stayed up late into night, playing, drinking and chatting, and then Dessner thought she went to bed. But the next morning, at around 9:00 am, Swift showed up and sang him a song she had written it in the middle of the night. "My brain exploded," he said, "because she sang it to me in my kitchen, and it was just surreal."
  
  Dessner added that he had written the music many years ago, without ever finding the right lyrics to go with it. "It meant something to me, and it felt like the perfect song finally found it," he said "There was a feeling in it, and she identified that feeling: That feeling of… 'The ache in you, put there by the ache in me.' I think everyone can relate to that. It's one of my favorites."