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. Written by Anonymous

Andy (Al Madrigal) guilts Will (David Walton) into agreeing to babysit Marcus (Benjamin Stockham) so Fiona (Minnie Driver) can go on a job interview, but the situation gets complicated when they receive a last-minute invitation to a once-in-a-lifetime charity pool party hosted by rap star Lil Jon (guest star as himself). Meanwhile, Fiona discovers that honesty isn't always the best policy when it comes to landing a job. Written by Anonymous

Will (David Walton) attempts a much-needed boy's night out with Andy (Al Madrigal), but complications arise, leaving Will to reach out to Marcus (Benjamin Stockham) in hopes of salvaging the evening. When Andy later becomes available, he attempts to track down Will, but instead winds up bonding over the joys of parenting with Fiona (Minnie Driver). Meanwhile, Andy and his reluctant wife Laurie (guest star Annie Mumolo) solicit Will to be godfather to their son Jonah. Written by Anonymous

Marcus (Benjamin Stockham) asks Will (David Walton) for advice on how he can get Hannah (guest star Cricket Wampler) to invite him to her upcoming birthday party. When that proves unsuccessful, Fiona (Minnie Driver) takes it to task with Joanne (guest star Andrea Anders), Hannah's mother, who also happens to be the queen bee of a group of neighborhood moms that she is trying to win over. Written by Anonymous

When Marcus starts hinting that Will and Fiona should start dating, Will does everything to set him straight. Meanwhile, Fiona gets advice from Dakota to get back into the dating scene, and seizes the opportunity by asking out her plumber.

With Fiona (Minnie Driver) putting in extra hours at work, Marcus (Benjamin Stockham) finally gets his own house key, but he quickly loses his mom's trust when Will (David Walton) 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 (guest star Adrianne Palicki), 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. Written by Anonymous

Will throws a poker night for his friends, but the event is hijacked by Fiona, who has no problem making herself at home with the guys. Meanwhile, Marcus goes on his first sleepover, but has a hard time adjusting with his peers.

Fiona runs a school project for Marcus' class; Will takes Marcus on a shopping spree.

Will invites Sam to a game night; Marcus feels apprehensive about his new baby sitter.

Marcus is thrilled when his father, Hugh, visits unexpectedly; Sam's work schedule impedes romance.

Will is torn between two commitments; going to Marcus's birthday party or attending Samantha's gala.

When Sam is forced to evacuate her apartment, Will lets her stay with him.

Will (David Walton) is completely heartbroken when Sam (guest star Adrianne Palicki) receives a job opportunity she can't refuse in New York, prompting Fiona (Minnie Driver) and Marcus (Benjamin Stockham) to try their best to comfort their friend. With her absence weighing on his mind, Will turns to Andy (Al Madrigal) for his sage advice in figuring out how to best move forward. Written by Anonymous