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.

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

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.

Andy and Laurie vacation apart, Fiona and Laurie have a Spa day staycation in San Francisco, while Will and Andy head to Las Vegas where Andy goes on a drunken spending spree on magic tricks until Laurie shows up to renew her vows with Andy. Meanwhile Marcus tries to read a romance novel to understand adult relationships to impress Shea.

Clay is trying to steal Shea away from Marcus, Meanwhile Liz feels there may be something strange about the relationship between Will and Fiona.

Will plays wing-man for Marcus, but Marcus wants to win Shea back at the school dance, Liz dumps Will after he defends Fiona, Marcus professes his love for Shea, Fiona and Will kiss.