Season 2
Episodes
S2 · E1 · 5 Aug 2025 · 29 min
The Engagement Party
Sylvia and Will navigate the new boundaries of their friendship now that Will is engaged to Jenna.
S2 · E2 · 5 Aug 2025 · 26 min
The Dinner Party
In an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner.
S2 · E3 · 12 Aug 2025 · 30 min
The Bachelor Party
Sylvia and Will's college friend swings into town for the bachelor party. Sylvia helps Will to come to terms with his relationship.
S2 · E4 · 19 Aug 2025 · 32 min
Fore!
Will advises Sylvia to go corporate. In San Diego, Will's plans with Jenna take an unexpected turn.
S2 · E5 · 26 Aug 2025 · 36 min
Jeopardy
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 · E6 · 2 Sept 2025 · 24 min
Road Trip
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 · E7 · 9 Sept 2025 · 35 min
The Office Party
Will helps Sylvia throw a party for Charlie's law firm. Charlie makes an announcement.
S2 · E8 · 16 Sept 2025 · 33 min
Young Darcy Mysteries
Sylvia gets hired to plan a major Hollywood party. Will finds an unlikely investor for his new bar. Charlie contemplates his professional future.
S2 · E9 · 23 Sept 2025 · 30 min
Boundaries
To avoid dealing with Charlie, Sylvia invites herself along on Will and Katie's adventure to the LA River.
S2 · E10 · 30 Sept 2025 · 40 min
Brett Coyote's Last Stand
Sylvia and Will's friendship hits a wall. Sylvia has a realization about her marriage. Will hears news about his bar.
Data and images from TMDB.