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, 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.

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

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

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

Tensions flare between Sylvia and Will at a housewarming party.

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

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.

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.

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

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

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

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

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