Actress Maddie Banks has landed the female lead in the new hit Broadway show Worst Case Scenario, but her elation is cut short when the son she gave up for adoption 26 years ago shows up, announcing that his adoptive mother has died.

After learning that Arlo is a virgin, Maddie pays her understudy Brittany (Kristin Chenoweth) to seduce him. But things go awry when, after the act, Arlo says he is in love with Brittany and makes plans to spend the rest of his life with her.

After Frank irritates Maddie by not putting her name in his "Tony Nomination Pool" with other limo drivers, Arlo wonders how they ever got along. This leads Frank, Thelma and Maddie to recall when the three of them met in the 1980s.