Ben decides to set Barry up on a blind date with his colleague, thinking that the two will have a lot in common. Barry, suspicious because Ben hasn't asked her out himself, becomes convinced that there must be something drastically wrong with her. When they finally meet, Barry proceeds to ask her a series of inappropriate questions to determine her faults, only to upset her and drive a wedge between her and Ben as well.

Meanwhile, Bobby and Jason are engaged in a heated game of "chest," which comes to a head while Jason is meeting with his boss at a fancy restaurant to discuss a possible promotion.