Season 2
Season 2 • 2025
⭐ 4.0 / 5
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
Sylvia and Will navigate the new boundaries of their friendship now that Will is engaged to Jenna.
2025-08-05 • 29 min
2. The Dinner Party
In an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner.
2025-08-05 • 26 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.
2025-08-12 • 30 min
4. Fore!
Will advises Sylvia to go corporate. In San Diego, Will's plans with Jenna take an unexpected turn.
2025-08-19 • 32 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!
2025-08-26 • 36 min
6. Road Trip
2025-09-02 • 24 min
7. The Holiday Party
2025-09-09 • 35 min
8. Young Darcy Mysteries
2025-09-16 • 33 min
9. Boundaries
2025-09-23 • 30 min
10. Brett Coyote's Last Stand
2025-09-30 • 40 min
