The song is really about the girl he likes and how she's obsessed with Frank Sinatra and how he feels like he can't compare to her unrealistic ideals. There's a lot of teenage angst; driving around looking for a parking spot (so they can make out where no one can see). It's really a song about how girls and especially teenage girls size guys up by comparing them to famous men, and the feelings of the song's unreliable narrator who literally believes his girlfriend is in love with Frank Sinatra and not him.
The song is really about the girl he likes and how she's obsessed with Frank Sinatra and how he feels like he can't compare to her unrealistic ideals. There's a lot of teenage angst; driving around looking for a parking spot (so they can make out where no one can see). It's really a song about how girls and especially teenage girls size guys up by comparing them to famous men, and the feelings of the song's unreliable narrator who literally believes his girlfriend is in love with Frank Sinatra and not him.