Season 2
(2025)
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.
Cast
Episodes
The Engagement Party 7.8
August 5, 2025
Sylvia and Will navigate the new boundaries of their friendship now that Will is engaged to Jenna.
The Dinner Party 7.7
August 5, 2025
In an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner.
The Bachelor Party 7.0
August 12, 2025
Sylvia and Will's college friend swings into town for the bachelor party. Sylvia helps Will to come to terms with his r…
Fore! 7.7
August 19, 2025
Will advises Sylvia to go corporate. In San Diego, Will's plans with Jenna take an unexpected turn.
Jeopardy 5.5
August 26, 2025
When Will moves in with Sylvia and Charlie, her new job forces the guys to spend one-on-one time together. Charlie goes…
Road Trip 6.7
September 2, 2025
Sylvia, Will, and Katie take a road trip to the desert. Will faces the reality of working for his ex-fiancée. Sylvia qu…
The Office Party 6.0
September 9, 2025
Will helps Sylvia throw a party for Charlie's law firm. Charlie makes an announcement.
Young Darcy Mysteries 7.0
September 16, 2025
Sylvia gets hired to plan a major Hollywood party. Will finds an unlikely investor for his new bar. Charlie contemplate…
Boundaries 7.0
September 23, 2025
To avoid dealing with Charlie, Sylvia invites herself along on Will and Katie's adventure to the LA River.
Brett Coyote's Last Stand 6.8
September 30, 2025
Sylvia and Will's friendship hits a wall. Sylvia has a realization about her marriage. Will hears news about his bar.