With the help of Chelsea Handler, Leah coaches her assistant Raffy on his dating skills when he lands a surprise date. After a makeover, a little waxing, and some blunt tips from Chelsea and Leah on talking to women; will Raffy's date be a success?

Leah finds out Angelo made a bad commercial for the family diner and he decides to film a new one; Leah tries auditioning for voice-over work and the results are hilarious.