Dorothy at Forty Lyrics

Lyric discussion by truthbealiar 

Cover art for Dorothy at Forty lyrics by Cursive

He's not speaking to the literal Dorothy from Wizard of Oz. Certainly, there's a lot of Wizard of Oz imagery in this and the other "Dorothy" song ("Dorothy Dreams of Tornados"), but he's using Dorothy to refer to dreamers who are too lazy or afraid to do anything to persue those dreams.