Back before facebook, when dial up was all the rage, there were message boards and group chat programs that required a username. I tried variations of my name and most were usually taken and i didn't want to use my name+12345, so I decided to be somewhat creative.
I love debate and would flip or flop on which side of the debate to argue just because and was studying psychology at that time in college so I came up with drdilemma as a username. My wife is interested in Geocaching and wanted to use one account. Since we are a team, TeamDilemma it is.