This week Patti has two of her youngest clients ever. Bill Clerico is a 25-year-old computer programmer who made his millions in Silicon Valley. Patti immediately realizes this "Baby Bill Gates" needs some dating confidence, and brings in the queen of sex appeal, Jenny McCarthy, to teach him some game. Patti's second client is 23-year-old trust fund baby Skylar Hauswirth. For Skylar it is all superficial, and Patti must take him under her wing to find him his first girlfriend.