Oberst adopts on this song the perspective of a contrite father, proud of his child's accomplishments despite his own shortcomings as a dad. "I definitely struggled with whether to put that one on the record," Oberst told Billboard magazine. "It has more sentimentality to it than any of the other songs, but I've seen a lot of friends go through that stuff. [Having kids] would be a cool thing to do someday. I don't particularly feel ready for it right now, but I guess no one ever does."
The song's music video was filmed on Fire Island, which is the 32-mile-long island that stretches south of New York's Long Island. Popular with the gay community, The Village People paid tribute to the location on their 1977 song "Fire Island."
The lyrics for Lesley Gore's "It's My Party" were based on actual events relating to his daughter Judy's sweet 16 party. The teenager threw a tantrum and burst into tears when her mum and dad insisted that her grandparents had to be invited.