(This ia around season 1/2 so Sam is 22 and Dean is 26 i think lol)

You, Sam and Dean were bored at the motel, so instead of watching a tv show or movie, or even cooking, y'all decide to play the most chaotic game ever...Truth or Dare.

Sam:"Ok, Dean truth or dare?"

Dean:"Hmm...Dare because I'm not a wuss."