After writing a hit song, Will is able to lead a life of leisure, free of financial woes; when a needy single woman and her charming 11-year-old son move in next door, Will's perfect life is impacted.

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.

Marcus hints that Will and Fiona should start dating; after Dakota (Leslie Bibb) gives her dating advice, Fiona asks out her plumber.

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.