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.
01. The Engagement Party
Sylvia and Will navigate the new boundaries of their friendship now that Will is engaged to Jenna.
29min
August 5, 2025
02. The Dinner Party
In an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner.
26min
August 5, 2025
03. 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.