Dean has had a warrant out for 'murder' for a few months now, He had done something stupid that got both him and you locked up and behind bars.

"You said you had a plan, how're you gonna get me outta these cuffs, stupid!" You shout at him in a hushed voice as you lean forward so no one else would hear.

"I do! I'm thinking..." Dean says, obviously not having a single thought on how to get out of prison.