A platonic pair of former best friends approaching midlife reconnect after a long rift. The duo’s friendship becomes more consuming—and destabilizes their lives in a hilarious way.
Where to watch
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Apple TV
see all options Availability data: JustWatch
- Seasons
- 3
- Episodes aired
- 20
- Latest aired
- S02E10
- Total runtime
- 10h 19min
Timeline when each season aired
- Season 1 May 2023 – July 2023 10 episodes
- the show was away for 2 years
- Season 2 August 2025 – September 2025 10 episodes
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S02E01 The Engagement Party
August 5 · 29min find the promo
Show synopsis
Sylvia and Will navigate the new boundaries of their friendship now that Will is engaged to Jenna.
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S02E02 The Dinner Party
August 5 · 26min find the promo
Show synopsis
In an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner.
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S02E03 The Bachelor Party
August 12 · 30min find the promo
Show synopsis
Sylvia and Will's college friend swings into town for the bachelor party. Sylvia helps Will to come to terms with his relationship.
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S02E04 Fore!
August 19 · 32min find the promo
Show synopsis
Will advises Sylvia to go corporate. In San Diego, Will's plans with Jenna take an unexpected turn.
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S02E05 Jeopardy
August 26 · 36min find the promo
Show synopsis
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!
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S02E06 Road Trip
September 2 · 24min find the promo
Show synopsis
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.
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S02E07 The Office Party
September 9 · 35min find the promo
Show synopsis
Will helps Sylvia throw a party for Charlie's law firm. Charlie makes an announcement.
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S02E08 Young Darcy Mysteries
September 16 · 33min find the promo
Show synopsis
Sylvia gets hired to plan a major Hollywood party. Will finds an unlikely investor for his new bar. Charlie contemplates his professional future.
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S02E09 Boundaries
September 23 · 30min find the promo
Show synopsis
To avoid dealing with Charlie, Sylvia invites herself along on Will and Katie's adventure to the LA River.
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S02E10 Brett Coyote's Last Stand
September 30 · 40min find the promo
Show synopsis
Sylvia and Will's friendship hits a wall. Sylvia has a realization about her marriage. Will hears news about his bar.