Season 2

01 The Engagement Party Episode 15th August 2025 Sylvia and Will navigate the new boundaries of their friendship now that Will is engaged to Jenna. 02 The Dinner Party Episode 25th August 2025 In an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner. 03 The Bachelor Party Episode 312th August 2025 Sylvia and Will's college friend swings into town for the bachelor party. Sylvia helps Will to come to terms with his relationship. 04 Fore! Episode 419th August 2025 Will advises Sylvia to go corporate. In San Diego, Will's plans with Jenna take an unexpected turn. 05 Jeopardy Episode 526th August 2025 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! 06 Road Trip Episode 62nd September 2025 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. 07 The Office Party Episode 79th September 2025 Will helps Sylvia throw a party for Charlie's law firm. Charlie makes an announcement. 08 Young Darcy Mysteries Episode 816th September 2025 Sylvia gets hired to plan a major Hollywood party. Will finds an unlikely investor for his new bar. Charlie contemplates his professional future. 09 Boundaries Episode 923rd September 2025 To avoid dealing with Charlie, Sylvia invites herself along on Will and Katie's adventure to the LA River. 10 Brett Coyote's Last Stand Episode 1030th September 2025 Sylvia and Will's friendship hits a wall. Sylvia has a realization about her marriage. Will hears news about his bar.