When Jimmy Met Greggy (S03E24)
When Greg mentions that Jimmy never does anything for him, Jimmy reminisces about their younger days in the 1980s, when he, Billy, and Brian were pizza delivery teens with questionable hairstyles, while Christine worked as a waitress at Howard Johnson's. Jimmy becomes furious upon hearing that Kim is visiting with her new boyfriend, Greg, knowing it will devastate Brian, Kim's ex from before college. Greg will also be crashing on Jimmy's couch. Upon meeting Greg, Jimmy can’t fathom what Kim sees in him. Brian unexpectedly shows up, pleading for Kim to return to him, and after she asks him to leave, he threatens Greg. Jimmy intervenes, promising to handle Greg himself, and takes him to a diner, where he discovers that Kim was Greg's first love. In a bid to intimidate Greg, Jimmy starts making up stories.