Based on the best-selling Nick Hornby novel, written/produced by Jason Katims and directed by Jon Favreau comes a different kind of coming-of-age story. Will Freeman lives a charmed existence as the ultimate man-child. After writing a hit song, he was granted a life of free time, free love and freedom from financial woes. He’s single, unemployed and loving it. So imagine his surprise when Fiona, a needy, single mom and her oddly charming 11-year-old son Marcus move in next door and disrupt his perfect world. To Will (David Walton) and Fiona’s (Minnie Driver) surprise, Shea (guest star Izabela Vidovic) accepts Marcus’ (Benjamin Stockham) proposal to be his girlfriend. However, Shea’s idea of a boyfriend translates closer to a personal assistant than a companion. Elsewhere, Fiona attempts to be more spontaneous with Chris (guest star Chris Diamantopoulos), while Will chaperones Marcus and Shea’s frozen yogurt date. With high hopes of meeting single women, Will and TJ go out to their favorite watering hole on Valentine’s Day. With help from the bartender, Liz, Will lands a date and oddly finds himself attending a cat party – but his heart is pulled elsewhere. Meanwhile, Marcus tries to plan the perfect Valentine’s date for Shea, but when things don’t go according to plan, Marcus turns to Chris for his sage advice in Will’s absence. Will starts teaching guitar lessons, but ends up having a fling with a student's mother. With the help of Andy, Will gets music mogul Johnny Idalis to listen to a new song he wrote, however Johnny isn't impressed with the hook. Meanwhile, Marcus grows upset and frustrated with Chris and Fiona's growing relationship and flees to crash with Will, who is left struggling to juggle writing a catchy hook and the complications of his new roommate. When Will learns Andy scored an invite to music mogul Johnny Idalis' son's Bar Mitzah, he sees an opportunity to get his music noticed and forces Andy to make him his plus one. With a push from Shea, Marcus convinces Fiona to let him stay home alone while she is on a date with Chris. During their night out alone, mischievous Shea takes Marcus party crashing while Andy and Will find themselves deep into a lie to impress Johnny.