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

Unnerved by the closeness of Will's relationship with Sylvia, Charlie invites Will to join him and his coworkers at a baseball game.

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

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

Frustrated by how much time Sylvia is spending with Will, Charlie crosses a line. Will confronts Reggie and Andy.

When Will moves in with Sylvia and Charlie, her new job forces the guys to spend one-on-one time together. Charlie goes on Jeopardy!

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

Will and the guys take Sylvia on a business trip to San Diego. Charlie grows more suspicious about Sylvia and Will's relationship.

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

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

Will introduces Sylvia to his much younger girlfriend, Peyton—then gets upset when Sylvia hires her as a babysitter.

Tensions flare between Sylvia and Will at a housewarming party.

In an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner.

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

Will accompanies Sylvia to an open house. Sylvia helps Will sneak into his ex-wife's home to get the rest of his stuff and make a clean emotional break.

While Sylvia's husband attends a conference, she spends the day getting drunk with Will—who informs her about a development with his bar.

Sylvia throws a divorce party for Will to cheer him up, but it gets out of hand when his rowdy friends try to take control of the night.

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.

After a long rift in their friendship, Sylvia reunites with her old best friend, the newly divorced Will.

Sylvia struggles to keep up with the brutal pace at her new law firm. Will learns about Reggie and Andy's new plans.