Dear John starred Judd Hirsch as easygoing Drake Prep high school teacher John Lacey who is dumped by his wife, Wendy, via a Dear John letter. Wendy ends up with everything in the divorce settlement, including custody of the couple's son, forcing John to move into an apartment in Ozone Park, Queens.

John soon joins the One-2-One Club, a self help group for divorced, widowed or lonely people. The group is led by Louise (Jane Carr), a sex-obsessed British woman. Other members of the group include Kate McCarron (Isabella Hofmann), a sweet divorcée, Kirk Morris (Jere Burns), a cocky ladies' man, Ralph Drang (Harry Groener), a shy and neurotic tollbooth collector, Bonnie Philbert (Billie Bird), a feisty senior citizen, and Tom, Mrs. Philbert's quiet boyfriend (Tom Willett).