On Christmas Eve, Cliff (Michael Strassner), a newly sober improv comedian, cracks a tooth and lands in the emergency care of Didi (Liz Larsen), an older no-nonsense dentist. What begins as a routine check-up sparks an unpredictable evening of misadventures. Together, Cliff and Didi fight to overcome being shut out by their families, face their biggest fears, and discover their own surprising and tender connection.