Leslie and staff watch in awe as City Councilman Bill Dexhart gives a public apology to his wife for engaging in sexual activity with a woman, a man and a stranger. Dexhart uses his birthday as a defense for committing the perverted acts. Mark wonders why anyone would want to be a politician: it just opens doors for people to find dirt on you. Tom claims he could run for office, he's squeaky clean!
The Dexhart sex scandal sparks a friendly competition between Tom, Mark, Donna, April, Jerry and Ron. Although Jerry doesn't want any part of it, Tom forces him. The name of the game: find the most dirt on your coworker! Ron wants to prove that he can find more dirt on Tom than Tom can find on him. April loves games that turn people against each other.
Leslie and Dave are a bit cutesy in the office. They have their first date planned for tomorrow night! During an interview, Leslie talks about how she is not nervous about the date, but then throws her phone across the room when it vibrates. Leslie's nerves may be kicking in! Mark tells Ann that he is trying to dig up dirt on his coworkers. Ann thinks it's good to see her hard-earned tax dollars at work.
Ann and Leslie have lunch. Ann finishes a story about how she saved someone's life and Leslie quickly changes the subject to the upcoming date with Dave. Leslie is really nervous, she has no idea what to wear: a sexy hat or cargo pants? Ann doesn't think Leslie should go with either. Ann offers to help Leslie find something to wear.
Tom doesn't think there is any way for his co-workers to find dirt on him. April and Donna search the Internet. Tom shreds all his receipts: he never leaves a paper trail. Ron bursts through and shows a picture of Tom in Taliban robes! Tom says that he was a Jedi for Halloween. Ron believes that some voters may think differently. Tom retaliates and reveals that Ron has been married twice and his second wife has the same name as the first: Tammy. Ron is not happy because Tom has just breached a "Jaeger secret."
Ann helps Leslie pick out an outfit. Leslie comes out in a pretty black dress that Ann really likes. Leslie then goes on to ask Ann a bunch of "what if" questions. Leslie thinks Dave may ask her questions that she won't be ready for. Ann tells Leslie to relax, but Leslie has a slew of questions she wants to go over, like, "What if my sleeves catch on fire?" Ann tells Leslie not to worry. However, Leslie has these concerns because they have all happened to her! Leslie lists her bad date experiences: drinking vinegar, 3-D glasses, and teeth pulling. Ann decides to fix Leslie's first date problems. The women will have a practice date!
Ann and Leslie meet at a bar and Ann pretends to be Dave. Ann gives Leslie hints on what not to do and is shocked when Leslie takes out note cards to spark conversation. In interview, Ann says that Leslie is in pretty bad shape. Leslie has just given a detailed history on the teeter-totter. Before Leslie can continue, Ann stops her. Ann directs Leslie to ask a question, Leslie blurts out, "How big is it?"
Tom's wife, Wendy, comes to pick him up at work. Tom has just dug up some dirt on Donna! Ron and Wendy meet again, and Tom confidently walks out with his super hot wife who just got super rich! Ron curiously watches them leave. Ron believes that Wendy's beauty, on a ten point scale, is 7.4, which is way too high for Tom, who is a 3.8.
Ann and Leslie start their practice date over again. This time, Ann acts as the worst date ever! First Ann gives Leslie attitude for being late ands says that Leslie's nipples are showing through her dress. Leslie is astonished! Ann, in interview, reveals her plan: she is going to get Leslie over her phobia of first dates by immersing Leslie in something called "exposure therapy." She is going to "immerse Leslie in a tank of bad date." Leslie stumbles over excuses about being late and spills flowers in Ann's soup. Leslie runs to the "whiz palace" or what some other people may refer to as the bathroom.
Back at the office the digging up dirt game is still on! Mark accidentally reveals that Jerry is adopted. Mark feels horrible! Ron finds out that Tom's wedding was a sham! It is a green card marriage. Wendy was born in Ottawa, Canada. Tom confesses. Ron knew it! Tom says that Ron can't turn him in, regardless of the game. Ron won't but he wants Tom to admit that Ron bested Tom in this game! Tom surrenders to Ron's demand! Later that night, Tom approaches Mark and asks him for assistance in digging up dirt on Ron. Mark gives Tom a name: Duke Silver.
The bad practice date between Ann and Leslie goes on. Ann pretends to be gross and terrible. Leslie gets angry and finally has a breakthrough. Afterward, Leslie and Ann go to a bar and have some celebratory drinks. Ann boosts Leslie's confidence and at the end of the night Leslie goes to Dave's house. Leslie, who is drunk, tells Dave that their first date is going to be awesome. Dave seems uncomfortable and Leslie invites herself in. Leslie confesses to Dave how she was panicked about the date and starts to come on strong. Dave decides to give an intoxicated Leslie a ride home.
Tom follows Mark's lead and goes to a bar to find Duke Silver. Moments later, Duke Silver, A.K.A. Ron comes out with a saxophone and plays some smooth jazz for the older women in the bar. He breaks out with "I Want to Know What Love Is." Tom takes a video with his phone. After Ron's set Tom approaches him. Ron and Tom decide to call a truce. Meanwhile Mark, inspired by the Dexhart scandal, goes to Ann's house and reveals all his skeletons to her.
The next morning, Dave visits Leslie at work and returns some of her clothes she left at his house. Dave accepts Leslie's apology and says that she can make it up to him tonight, on their second date! Leslie nailed the first date! Meanwhile, April is upset no one has uncovered dirt about her.