13. Anna Howard Shaw Day

Complete story — includes the ending

Liz schedules a needed root canal on Valentine's Day to avoid feeling lonely on the holiday. She realizes she will need someone to escort her home from the dentist's office due to the after effects of anaesthesia. She asks her colleagues for a ride home, but they cannot do it. Meanwhile, Jack meets a successful and attractive CNBC host named Avery Jessup ( Elizabeth Banks ) and ponders the possibility of having a relationship with her as he realizes that Nancy will not get divorced. They eventually embark on a number of both successful and unsuccessful dates. Elsewhere, Jenna is saddened that her stalker ( Horatio Sanz ) loses interest in her as he was the longest relationship she has ever had. Liz goes to her appointment and after her surgery she reassures the staff that the anaesthesia is having no effect on her and can take herself home. Liz sees her former boyfriends Drew Baird ( Jon Hamm ), Dennis Duffy ( Dean Winters ), and Floyd DeBarber ( Jason Sudeikis ) but in fact is hallucinating and mistakes the three for the three women dental assistants. One of them calls Jack asking if he could come pick up Liz and take her home, which he does.