Will returns to sort out a few things but ends up staying longer than planned when he sees Marcus's new "friends".

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.

Will orchestrates his yearly halloween extravaganza and fiona finally lets her hair down.

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

Will is sued by an angry ex-girlfriend.

Marcus is cast as Romeo by a new teacher in a school production featuring Shakespeare scenes.

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. Meanwhile, Dakota helps Fiona prepare for a night of intimacy with Chris.

Will accompanies Andy to the Bar Mitzvah of a music mogul's son.

Music mogul Johnny Idalis listens to Will's new song, but wants him to improve the hook. Marcus is frustrated with his mother's burgeoning relationship and leaves to crash with Will.

Looking to make some quick cash, Will decides to start teaching guitar lessons. However, after a fling with his student's mom, Emma, Andy speculates that Will is being paid for more than just his musical expertise. Elsewhere, Fiona finds herself suddenly accepted by the popular moms at school and Marcus prepares to perform at the upcoming school fundraiser.

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.

Will and TJ go out on Valentine's Day, hoping to meet single women. Marcus turns to Chris.