Outkicking your Coverage
To engage in a romantic relationship with a person who is much better looking, and/or smarter, and/or in a higher socioeconomic class than you. Essentially, a person who is widely considered to be 'out of your league.'
Bob: Your new girlfriend is smokin' hot... A legitimate '8'... How do you continue to keep outkicking your coverage.
Other guy, also named Bob: I have an extremely large penis!
Other guy, also named Bob: I have an extremely large penis!