10 episodesFirst aired 5 August 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.
E1Aug 202529m
Sylvia and Will navigate the new boundaries of their friendship now that Will is engaged to Jenna.
E2Aug 202526m
In an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner.
E3Aug 202530m
Sylvia and Will's college friend swings into town for the bachelor party. Sylvia helps Will to come to terms with his relationship.
E4Aug 202532m
Will advises Sylvia to go corporate. In San Diego, Will's plans with Jenna take an unexpected turn.
E5Aug 202536m
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!
E6Sept 202524m
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.
E7Sept 202535m
Will helps Sylvia throw a party for Charlie's law firm. Charlie makes an announcement.
E8Sept 202533m
Sylvia gets hired to plan a major Hollywood party. Will finds an unlikely investor for his new bar. Charlie contemplates his professional future.
E9Sept 202530m
To avoid dealing with Charlie, Sylvia invites herself along on Will and Katie's adventure to the LA River.
E10Sept 202540m
Sylvia and Will's friendship hits a wall. Sylvia has a realization about her marriage. Will hears news about his bar.