Hearing England Dan & John Ford Coley's "It's Sad To Belong" on the radio for the first time in years yesterday got me thinking. While its general sentiment of longing isn't unusual for a pop song, the resigned wistfulness of the song's premise stands out. The protagonist wishes he could get into a time machine and choose to be with someone who seems perfect for him now; he goes home, however, to someone else he once thought was the one. There's no trace of anger or bitterness in his acknowledgment of this, however--just an admission that the choices we make are based on the options we have and how we feel at the time.
I still think that's one of the braver admissions I've heard in a pop song.