This song is about being in a relationship with an alcoholic girlfriend.
Lead singer Travie McCoy said at the time of this song's release: "I find myself a lot of times in relationships with females who consume a lot of alcoholic beverages. There's this old saying that you'll eventually marry your mother. As weird as that sounds, it's like you're going to marry someone that's pretty much your mom and my mom's an alcoholic and I find that I get into these situations with these females and I would see these similarities that would freak me out. So that song kind of helped me get through that situation. At the same time, it's just this unspoken thing that I have an attraction to girls who are just like, "Let's get wasted!" I'm out of that phase now. My girlfriend is straight-edge."