Roy's date with a woman goes horribly wrong after she mistakes some chocolate on his head for faeces. Despite Roy's insistence that "it's not shit", he declares that the woman didn't like him because women only like "bad boys" and devises a plan to prove his theory by posting a despicable singles ad. After getting many responses, Roy arranges a date with a surprisingly good-looking woman and sets out to act like a "bastard" to progress their relationship. Jen impresses a company security guard by correctly guessing obscure facts; she is later selected as his "phone a friend" on the quiz show Who Wants to Be a Millionaire?. The security guard asks her out, following which Jen is unable to answer the quiz question correctly. Roy and Jen then take their dates to the same restaurant on Moss' recommendation. Following a scene in which a restaurant entertainer is assaulted by Jen's date after mocking him for failing on Millionaire, Roy and Jen's dates leave together.