Seasons & episodes

S2 · E1The Engagement Party 2025-08-05 · 29 min＋

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

S2 · E2The Dinner Party 2025-08-05 · 26 min＋

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

S2 · E3The Bachelor Party 2025-08-12 · 30 min＋

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

S2 · E4Fore! 2025-08-19 · 32 min＋

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

S2 · E5Jeopardy 2025-08-26 · 36 min＋

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!

S2 · E6Road Trip 2025-09-02 · 24 min＋

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.

S2 · E7The Office Party 2025-09-09 · 35 min＋

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

S2 · E8Young Darcy Mysteries 2025-09-16 · 33 min＋

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

S2 · E9Boundaries 2025-09-23 · 30 min＋

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

S2 · E10Brett Coyote's Last Stand 2025-09-30 · 40 min＋

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