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.

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.

Will is convinced that Chris is cheating on Fiona so he follows Chris to a hotel, where Chris reveals he has accepted a job offer out of the country, while Fiona prepares to tell Chris she loves him. Meanwhile, Marcus is trying to raise enough money to take Shea on a date to the movies so Marcus sells his silence to Andy for $100.