The boys of The All-American Rejects said that this song is about a girl who left the guy because he was not serious enough about growing up and becoming a business man. This part can be seen in the first few lines of "I wake up every evening,With a big smile on my face And it never feels out of place
And your still probably working at a 9 to 5 pace. I wonder how bad that tastes"

It can be seen that he has not changed his ways and is glad to not be with someone who is trying to change him. It then goes to state that he is truly happy with his fun carefree life but questions her money driven lifestyle. "Now where's that picket fence, love. And where's that shiny car,
And did it ever get you far?"

The main point of the song is to say that he is now successful but still living his life the way he wants too. She left him because she saw him as being immature. He is hoping that this fact drives her crazy and "gives you hell."