Season 2
10 episodes · Aug 5, 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.
Season Videos
0/10 watched
Swipe a row to mark watched · long-press to mark up to there
S2E1The Engagement Party
Aug 5, 202529mSylvia and Will navigate the new boundaries of their friendship now that Will is engaged to Jenna.
S2E2The Dinner Party
Aug 5, 202526mIn an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner.
S2E3The Bachelor Party
Aug 12, 202530mSylvia and Will's college friend swings into town for the bachelor party. Sylvia helps Will to come to terms with his relationship.
S2E4Fore!
Aug 19, 202532mWill advises Sylvia to go corporate. In San Diego, Will's plans with Jenna take an unexpected turn.
S2E5Jeopardy
Aug 26, 202536mWhen Will moves in with Sylvia and Charlie, her new job forces the guys to spend one-on-one time together. Charlie goes on Jeopardy!
S2E6Road Trip
Sep 2, 202524mSylvia, 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.
S2E7The Office Party
Sep 9, 202535mWill helps Sylvia throw a party for Charlie's law firm. Charlie makes an announcement.
S2E8Young Darcy Mysteries
Sep 16, 202533mSylvia gets hired to plan a major Hollywood party. Will finds an unlikely investor for his new bar. Charlie contemplates his professional future.
S2E9Boundaries
Sep 23, 202530mTo avoid dealing with Charlie, Sylvia invites herself along on Will and Katie's adventure to the LA River.
S2E10Brett Coyote's Last Stand
Sep 30, 202540mSylvia and Will's friendship hits a wall. Sylvia has a realization about her marriage. Will hears news about his bar.