Season 2
10 episodes · 2025
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.
1The Engagement Party
Sylvia and Will navigate the new boundaries of their friendship now that Will is engaged to Jenna.
2The Dinner Party
In an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner.
3The 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.
4Fore!
Will advises Sylvia to go corporate. In San Diego, Will's plans with Jenna take an unexpected turn.
5Jeopardy
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!
6Road 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.
7The Office Party
Will helps Sylvia throw a party for Charlie's law firm. Charlie makes an announcement.
8Young 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.
9Boundaries
To avoid dealing with Charlie, Sylvia invites herself along on Will and Katie's adventure to the LA River.
10Brett 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.