Howard brought Andrea back in to play "Who's Smarter than Miss Howard Stern?" and she said that her new reality show was exactly what she needed to slow down her drinking. Howard then welcomed today's competitors, Siobhan and Rick, noting that they both looked very masculine. Rick confessed that he was there because he wanted to propose to his girlfriend, but he lost $20,000 when he invested in a vitamin store that went bust.
Howard welcomed Sabine, Rick's girlfriend, to the studio, and she reported that she wanted to be married to Rick without sacrificing financial security. Andrea asked Siobhan if her/his sex change was to become a man or a woman, so Howard asked her to guess. Andrea guessed Siobhan had become a woman, and Howard told her she was correct. Howard then explained the rules of the game and asked the first question:
What is the First Lady's first name? Siobhan: No. Rick: Also no. Oddly, Andrea knew it was "Laura."
Who was Bill Clinton's vice president? Siobhan: No. Rick: No. Andrea guessed "Cheney," so both contestants earned a point.
What is Lance Armstrong famous for? Siobhan: No. Rick: Yes. Andrea guessed, "going to the moon," so Siobhan earned a point.
Which White House intern did Bill Clinton have an affair with? Siobhan: No. Rick: No. Andrea knew it was Monica Lewinsky.
What is nine times nine? Siobhan: No. Rick: Yes. Andrea guessed "90," scoring another point for Siobhan.
What were the last two states to join the United States? Siobhan: No. Rick: No. Andrea guessed "Canada and Hawaii."
What is the name of the black candidate running for president? Siobhan: No. Rick: No. Andrea knew it was Obama, proving both contestants wrong.
What is cannabis? Siobhan: Yes. Rick: Yes. Andrea guessed "a meat-eater."
What is the closest planet to the sun? Siobhan: No. Rick: No. Andrea guessed "Earth."
Who was the mayor of NYC during 9/11? Siobhan: No. Rick: No. Andrea knew it was Rudy Giuliani.
What country is the United States currently at war with? Siobhan: Yes. Rick: No. Andrea knew it was "Iraq," scoring another point for Siobhan.
A doctor who specializes in the anus and rectum is called what? Siobhan: No. Rick: Yes. Andrea guessed "Gynological," scoring another point for Siobhan and knocking Rick out of the contest.
Howard congratulated Siobhan on "her" win and said he wished "her" brother would see some of the money "she" owes him. Siobhan claimed "she" wouldn't ask Howard for money again "for a year," but Gary predicted "she" would break that promise by March. Howard then asked Sabine, Rick's girlfriend, if she'd like to make up for Rick's loss by getting naked for $1,000, but she wouldn't even strip down to a bathing suit.