Can anyone help me find the name of a show from the turn of the decade that was kind of a musical possibly set in the 50s? I have this scene in my head of a girl singing "my boyfriend's back." it's really bugging me.

Well you really didn't give enoug details, but there was a 1993 movie called My Boyfriend's Back, and three sitcoms had the title for one of their episodes. Those are Facts Of Life, Mad About You and Saved By The Bell. All of those are from around the time you're talking about, so take your pick, although none of those were really set in the 50's

Grabbing at straws, but was it Rags To Riches with Joe Bologna or Just The Ten of Us (a spin-off of Growing Pains)?