Never Again (2002)

Synopsis
Two singles in their early fifties who are convinced love has passed them by find each other -- and then try to figure out what to do next -- in this romantic comedy. Grace Minor (Jill Clayburgh) is a social worker whose personal life has hit the skids. Prompted by her friends Natasha (Sandy Duncan) and Elaine (Caroline Aaron), Grace takes the plunge and sets up a meeting with a man she's found through an Internet dating service. The date is a complete disaster, and Grace, deciding she needs a stiff drink, dashes into the first watering hole she finds. Grace finds herself in a gay bar, where she meets Christopher Roland (Jeffrey Tambor), a full-time exterminator and part-time jazz musician who, after an unsatisfying relationship with a younger woman and a surprising erotic dream, thinks he might be turning gay. Christopher and Grace strike up a conversation and quickly discover they have a great deal in common. They begin dating, but both have been through enough bad relationships in the past that they are determined not to get too serious about this one, even after they discover they get along extremely well in bed. Never Again also features Michael McKean as a cheerful transvestite prostitute and Bill Duke as one of Christopher's bandmates. ~ Mark Deming, All Movie Guide