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.

Jimmy hires Gerald as the new host at his restaurant and gives him a crash course in hospitality. Meanwhile, Vanessa teaches Sara how to take sexy photos for Bruce (guest star Andy Daly), and Annelise encourages Ravi to crack down on the comedy in the kitchen.