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New York "date doctor" Alex Hitchens (WILL SMITH) tries to charm gossip columnist Sara Melas (EVA MENDES) at the same time he is coaching shy Albert (KEVIN JAMES) on how to win the love of beautiful heiress Allegra Cole (AMBER VALLETTA).

When a young woman's pregnant, unmarried mother moves into her apartment, she does what any dutiful child with an expectant widow on her hands would do: she sets her up with every bachelor in town.