A confirmed bachelor, Don Johnston is dumped by his latest girlfriend, Sherry. Once again he resigns himself to living alone. But the delivery of a mysterious, anonymous letter forces him to take stock of his past. One of his exes informs him that he has a nineteen-year-old son who has set out to find him. Don’s best friend, Winston, a contented father and amateur sleuth, pushes him into investigating this ‘mystery.’ Despite his lack of interest in travel, Don sets off in search of evidence, catching up with four of his ex-girlfriends. His surprise visits to these unique women confront him with his past and, through this, with his present.