This song is about a guy who is frustrated with a girl who he needs "like a bad habit." He is frustrated that she turned him into what he is now: "Well my best side was your worst invention." He keeps asking her why won't she ever be happy and is determined not to come back down and stoop to her level.
Taking Back Sunday's song titles often have nothing to do with the songs themselves. In this case, the title comes from a bet made between the band and their guitarist Eddie Reyes. The bet was that he couldn't lose enough weight to slim down to 180 pounds by summer.
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