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.
Season cast
Episodes
10 in this season
1. The Engagement Party
7.9Sylvia and Will navigate the new boundaries of their friendship now that Will is engaged to Jenna.
2025-08-0529 min
2. The Dinner Party
8.3In an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner.
2025-08-0526 min
3. 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.
2025-08-1230 min
4. Fore!
8.0Will advises Sylvia to go corporate. In San Diego, Will's plans with Jenna take an unexpected turn.
2025-08-1932 min
5. 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!
2025-08-2636 min
6. Road Trip
7.4Sylvia, 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.
2025-09-0224 min
7. The Office Party
Will helps Sylvia throw a party for Charlie's law firm. Charlie makes an announcement.
2025-09-0935 min
8. Young Darcy Mysteries
7.6Sylvia gets hired to plan a major Hollywood party. Will finds an unlikely investor for his new bar. Charlie contemplates his professional future.
2025-09-1633 min
9. Boundaries
7.6To avoid dealing with Charlie, Sylvia invites herself along on Will and Katie's adventure to the LA River.
2025-09-2330 min
10. Brett Coyote's Last Stand
7.5Sylvia and Will's friendship hits a wall. Sylvia has a realization about her marriage. Will hears news about his bar.
2025-09-3040 min