"Jester's Night: Seriously Off Nut" tells us a story that happened the day before - The New Year. It is the time when we wait for the wishes to come true. The picture is about our dreams that change with time and, unfortunately, become more pragmatic. The characters dedicate their lives to the career without noticing anything around them even their lovers' worries. Living this day together with characters, a viewer understands that it is never too late to implement in life their dreams. A businessman and a housewife; a cab driver and a man-hater; a secretary and a barbershop; a director and an ordinary tutor - everyone has their own New Year. For someone it is a pleasant fuss and an opportunity to make a secret wish. For others it is an annual tradition to make fun of oneself and to laugh at others during "Jester's Night".
Maggie (Natalie Hall) and Jack (Evan Williams) are childhood family friends and now as adults give dating advice together on their popular local radio show. When they find out their show is being shopped around for national syndication, their boss encourages them to introduce their significant others to their families for a live, on-air New Year’s Eve special. Knowing their fathers’ local jazz club, The Magnolia, is struggling financially, Maggie and Jack agree to the special as long as it’s hosted at the club. But when Maggie and Jack are both dumped before the big event, Jack suggests they pretend to be a couple and surprise their listeners with the news during a midnight kiss on New Year’s Eve!
Though a childhood bout with polio left him dependent on an iron lung, Mark O'Brien maintains a career as a journalist and poet. A writing assignment dealing with sex and the disabled piques Mark's curiosity, and he decides to investigate the possibility of experiencing sex himself. When his overtures toward a caregiver scare her away, he books an appointment with sex surrogate Cheryl Green to lose his virginity.