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In a quest to find his own Amal Clooney, Jimmy goes out with Sara's co-worker, but when she is not impressed with his smooth moves, Jimmy turns to Sara for pointers. Meanwhile, Gerald and Vanessa decide to become friends with benefits.
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.