When Gerald can't make it in time for Edie's interview at the most elite pre-school in the area, Jimmy steps in to help out. But once he meets the admissions counselor (Joanna Garcia Swisher), he accidentally starts a lie that takes on a life of its own.

In hopes of helping Gerald score with the ladies, Jimmy takes him out for a swanky night on the town. But when Gerald falls for a party girl (guest star Lyndsy Fonseca), Jimmy fears she may be into Gerald for the wrong reasons. Meanwhile, Vanessa starts a mentorship with Annelise.