Season 2
Overview
Season two picks up with everyone's favorite pair of best friends as they contend with new midlife hurdles, including work, weddings and partners in crises. The duo tries their best to be each other's rock — but sometimes rocks break things.
Episodes
1. The Engagement Party
2025-08-05
Sylvia and Will navigate the new boundaries of their friendship now that Will is engaged to Jenna.
2. The Dinner Party
2025-08-05
In an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner.
3. The Bachelor Party
2025-08-12
Sylvia and Will's college friend swings into town for the bachelor party. Sylvia helps Will to come to terms with his relationship.
4. Fore!
2025-08-19
Will advises Sylvia to go corporate. In San Diego, Will's plans with Jenna take an unexpected turn.
5. Jeopardy
2025-08-26
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!
6. Road Trip
2025-09-02
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.
7. The Office Party
2025-09-09
Will helps Sylvia throw a party for Charlie's law firm. Charlie makes an announcement.
8. Young Darcy Mysteries
2025-09-16
Sylvia gets hired to plan a major Hollywood party. Will finds an unlikely investor for his new bar. Charlie contemplates his professional future.
9. Boundaries
2025-09-23
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
2025-09-30
Sylvia and Will's friendship hits a wall. Sylvia has a realization about her marriage. Will hears news about his bar.