Season 2

Directed by Nicholas Stoller · Francesca Delbanco

2025▶ Trailer

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.

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E1. The Engagement Party

Aug 5, 2025 · 29m

Sylvia and Will navigate the new boundaries of their friendship now that Will is engaged to Jenna.

E2. The Dinner Party

Aug 5, 2025 · 26m

In an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner.

E3. The Bachelor Party

Aug 12, 2025 · 30m

Sylvia and Will's college friend swings into town for the bachelor party. Sylvia helps Will to come to terms with his relationship.

E4. Fore!

Aug 19, 2025 · 32m

Will advises Sylvia to go corporate. In San Diego, Will's plans with Jenna take an unexpected turn.

E5. Jeopardy

Aug 26, 2025 · 36m

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!

E6. Road Trip

Sep 2, 2025 · 24m

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.

E7. The Office Party

Sep 9, 2025 · 35m

Will helps Sylvia throw a party for Charlie's law firm. Charlie makes an announcement.

E8. Young Darcy Mysteries

Sep 16, 2025 · 33m

Sylvia gets hired to plan a major Hollywood party. Will finds an unlikely investor for his new bar. Charlie contemplates his professional future.

E9. Boundaries

Sep 23, 2025 · 30m

To avoid dealing with Charlie, Sylvia invites herself along on Will and Katie's adventure to the LA River.

E10. Brett Coyote's Last Stand

Sep 30, 2025 · 40m

Sylvia and Will's friendship hits a wall. Sylvia has a realization about her marriage. Will hears news about his bar.