Though best friends, Shawn and Cory are almost complete opposites of one another. Outwardly, Shawn is a rebel, giving him more of a "bad boy" reputation and a popularity boost; he is occasionally given to stormy emotional outbursts, but his closest friends know that these are due mainly to his familial circumstances, having lived much of his life with little or no parental guidance.

Beginning in his middle school years Shawn is a skirt-chaser, usually never staying in a relationship long