When two sides both say there's is better, bigger, faster, longer, harder, whatever than the other side's.
"DSW" trivializes the competition as each side saying "My dick's bigger than yours."
A person who wears a Hawaiian style button up shirt that has dragons and/or a flame design all over it. A DSW usually starts as early as high school when they can afford to buy their own deck Magic the Gathering playing cards, this can evolve into Dungeons and Dragons later in life.
Me: "Wow man I've never seen any tits interested in Jon before."
Roommate: "Yeah, he really dropped that whole DSW stage that he had going in high school."