Will Freeman is a 38-year-old shallow, wealthy and irresponsible playboy, who has no surviving family and lives alone in a roomy, elegant London apartment. He's never had a job in his life because he lives well off the royalties from "Santa's Super Sleigh," a Christmas song his father wrote years ago. He's had lots of girlfriends, but he always dumps them within a few weeks. One day he realizes that his friends are all involved with the responsibilities of married life and that leaves him alone in the cold.
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Will is a bored swinger who dumps woman after woman, and after his late test break-up with a girl named Angie who was a single mom. He develops a theory about dating single mothers: "Passionate sex. A lot of ego massage. And a guilt-free parting." He then attends S.P.A.T. - Single Parents, Alone Together in order to meet emotionally fragile women. He charms a single mom named Suzie and poses as a single father with a two-year-old son named Ned himself. .
Through Suzie he meets a young needy cad named Marcus, who manages to work his way into Will's life. Marcus's single mom is a depression case and he just wants her to be happy, because since her late test break-up, she's been suicidal. At first, Marcus hopes to match Will up with his mother, but they aren't attracted to each other. However, Will and Marcus gradually bond. First Will tries to turn him away from his home but Marcus uses blackmail with threats that he'll spill to everyone that he is really a swinging bachelor who has no kid. They become television buddies at first until Will becomes a mentor to the kid.
About the boy. Marcus is a seriously confused kid that gets teased at school for singing out loud spontaneously. So it's no surprise that Will begins to help Marcus to act a little more masculine. And the he helps Will win dates with other single moms, too, by acting as his stand-in kid. Then Marcus gets a girl-friend at school and gains respect from some other students.