Ted proposes a road trip with Marshall to their favorite pizza parlor in Chicago to reminisce their bachelor days, but Lily wants in on the trip. Barney is seeking US citizenship for Robin, but her Canadian traits still remain.
Marshall and Lily desperately try to have a double date with Barney and Robin. Girls suddenly appear at Ted's apartment just to find a place to sleep in, making him a "Sexless Innkeeper."
When Robin fears that Barney is cheating on her, she soon discovers that he is spending his evenings with Ted learning everything there is to know on how to date her.
Ted discovers he had been fixed up with the same woman, seven years earlier. The rest of the gang goes to the Lusty Leopard strip club and see a dancer who looks like Lily.
When the gang finds out that Barney and Robin are hesitant to define their relationship, Lily forces them to confront their biggest fear...becoming boyfriend/girlfriend. Meanwhile, Ted is anxious about teaching his first lecture.