This song is sang from the point of view of a former high school lover of ambitious LA actress Dorothea, a character Swift created. He looks back at some happy memories of their teenage romance and laments "a tiny screen's the only place I see you now." Even though it's been years since their relationship, the guy still loves her; he tells Dorothea if she ever tires of Hollywood, "It's never too late to come back to my side."
The song mirrors the Christmas tryst between Dorothea and her former high school boyfriend that Swift recounts in "'Tis the Damn Season." This track takes place some years later when the aspiring actress has finally made it.
While the guy still loves his former high school sweetheart in this song, Dorothea also laments their lost relationship in "'Tis the Damn Season," but because they both have their own lives now in separate cities, their love will stay unrequited.
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