After writing a hit song, Will Freeman (David Walton) was granted a life of free time, free love and freedom from financial woes. He is single, unemployed and loving it. But when Fiona (Minnie Driver), a needy, single mom and her oddly charming 11-year-old son, Marcus (Benjamin Stockham), move in next door, his perfect life is about to hit a major snag.

Will gets an invitation to a pool party hosted by Lil Jon, but has already committed to watching Marcus; Fiona learns telling the truth isn't always the best way to get a job.

Will's night out with Andy does not go as planned, forcing Will to reach out to Marcus for help; Andy's wife, Laurie, reluctantly agrees to ask Will to be the godfather of their son.

Marcus turns to Will for advice on getting invited to a party, but when that doesn't yield results, Fiona gets involved.

When Marcus starts hinting that Will and Fiona should start dating each another, Will does everything in his power to set him straight. Meanwhile, Fiona gets advice from Dakota to get back into the dating scene, and with very little game, seizes the opportunity by asking out her plumber - with results she didn't quite anticipate.

With Fiona putting in extra hours at work, Marcus finally gets his own house key, but he quickly loses his mom's trust when Will has to rush him to the emergency room following an untimely incident with a knife. However, Marcus' misfortune has a silver lining for Will when he crosses paths with Dr. Samantha Lake, a beautiful and charming doctor who comes to Marcus' aid. Will is instantly smitten and stops at nothing in his attempts to win her over - even if it means bending the truth.