Season 2

Sylvia and Will navigate the new boundaries of their friendship now that Will is engaged to Jenna.

Sylvia and Will's college friend swings into town for the bachelor party. Sylvia helps Will to come to terms with his relationship.

Will advises Sylvia to go corporate. In San Diego, Will's plans with Jenna take an unexpected turn.

Sylvia, Will, and Katie take a road trip to the desert. Will faces the reality of working for his ex-fiancée. Sylvia questions Charlie's stability.

Will helps Sylvia throw a party for Charlie's law firm. Charlie makes an announcement.

Sylvia gets hired to plan a major Hollywood party. Will finds an unlikely investor for his new bar. Charlie contemplates his professional future.

To avoid dealing with Charlie, Sylvia invites herself along on Will and Katie's adventure to the LA River.

Sylvia and Will's friendship hits a wall. Sylvia has a realization about her marriage. Will hears news about his bar.