When Jack is assigned the job of Limo Driver, he jumps on the opportunity to relive his teen years of partying and excess. But chauffeuring kids to and from their proms doesn't turn out to be the wild ride Jack expected; far from accepting his attempts at showing them a good time, the kids mock Jack for being way too old to be such a try-hard.
Defeated and feeling his age, Jack turns to fellow limo driver, Devon, for advise. Devon tells Jack that the only way to lessen the beatings is to act with refinement, and hope the kids follow suit.
Meanwhile, Bobby revisits his past as well; his high school crush, Haley, approaches him to DJ the upcoming prom.