Will returns to San Francisco to sort out his finances after a surprising royalty check. Andy reveals to him that his wife Laurie might be pregnant and he needs Will's help to find out. Meanwhile, Marcus's new "friends" don't sit well with Will and he attempts to convince Fiona that the kids are up to no good.

Will is told to sell his San Francisco home in order to solve his money issues. So he decides to find Marcus a brand new best friend.

Despite not liking Halloween, Fiona attends Will's annual party. Will attempts to show Marcus the joys of Halloween.

Marcus develops a crush on a girl who has a penchant for trouble.

Will ends up being sued by an angry ex-girlfriend, Stacy, who is claiming she co-wrote his song "Runaway Sleigh". Will hopes that Fiona can help him persuade her to drop the lawsuit.

Marcus is ecstatic when a popular new teacher, Mr. Chris casts him as Romeo in the school production of notable Shakespeare scenes. Marcus asks Will to build the balcony set for his scene, however Will is more interested in watching "The Three Stooges" marathon with Marcus instead. Threatened by Mr. Chris' growing relationship with Marcus, Will tries to impress them with the construction of his balcony. Elsewhere, Mr. Chris not only has gained a fan in Marcus, but Fiona as well.

Feeling nervous about her first real date with Mr. Chris, Fiona wants Dakota to come with her as her safety net. Will ends up tagging along as well as he attempts to woo Dakota.

The Christmas celebrations are now in full swing but Will is not having a good time. With the lawsuit still pending, Laurie advises him to settle and move on with his life. Fiona and Andy attempt to create the perfect white Christmas for Marcus.

To celebrate a year of friendship, Marcus convinces Will to take him to the Golden Gate FemFest. Much to his chagrin, Will obliges and attempts to sneak backstage to fulfill Marcus' dreams of meeting Lisa Loeb, who is headlining the festival. Meanwhile, Dakota helps Fiona prepare for a night of intimacy with Chris.

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.

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.

Will starts to teach guitar in order to make some extra money but Andy soon starts to suspect that he is getting paid for more than guitar lessons.

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.

To Will and Fiona's surprise, Shea accepts Marcus' 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, while Will chaperones Marcus and Shea's frozen yogurt date.