Episode Rankings

1. #1 Fan Favorite
   

   7.4/10(388 votes)

   #1 - The Engagement Party

   S2:E18/5/2025

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

   Director:Nicholas Stoller

   Writers:Francesca Delbanco, Nicholas Stoller

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   Director:Nicholas Stoller

   Writers:Francesca Delbanco, Nicholas Stoller
2. 

   7.4/10(358 votes)

   #2 - The Dinner Party

   S2:E28/5/2025

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

   Director:Nicholas Stoller

   Writer:Ron Weiner

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   Director:Nicholas Stoller

   Writer:Ron Weiner
3. 

   7.6/10(371 votes)

   #3 - The Bachelor Party

   S2:E38/12/2025

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

   Director:Francesca Delbanco

   Writer:Justin Nowell

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   Director:Francesca Delbanco

   Writer:Justin Nowell
4. 

   8.1/10(368 votes)

   #4 - Fore!

   S2:E48/19/2025

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

   Director:Francesca Delbanco

   Writer:Andrew Gurland

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   Director:Francesca Delbanco

   Writer:Andrew Gurland
5. 

   7.6/10(335 votes)

   #5 - Jeopardy

   S2:E58/26/2025

   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!

   Director:Nicholas Stoller

   Writer:Alexandra Rushfield

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   Director:Nicholas Stoller

   Writer:Alexandra Rushfield
6. 

   7.3/10(306 votes)

   #6 - Road Trip

   S2:E69/2/2025

   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.

   Director:Francesca Delbanco

   Writer:Judy Choi

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   Director:Francesca Delbanco

   Writer:Judy Choi
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7. 

   7.6/10(295 votes)

   #7 - The Office Party

   S2:E79/9/2025

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

   Director:Francesca Delbanco

   Writer:Francesca Delbanco

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   Director:Francesca Delbanco

   Writer:Francesca Delbanco
8. 

   7.5/10(291 votes)

   #8 - Young Darcy Mysteries

   S2:E89/16/2025

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

   Director:Francesca Delbanco

   Writer:Francesca Delbanco

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   Director:Francesca Delbanco

   Writer:Francesca Delbanco
9. 

   7.4/10(294 votes)

   #9 - Boundaries

   S2:E99/23/2025

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

   Director:Nicholas Stoller

   Writer:Francesca Delbanco

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   Director:Nicholas Stoller

   Writer:Francesca Delbanco
10. 

    7.6/10(284 votes)

    #10 - Brett Coyote's Last Stand

    S2:E109/30/2025

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

    Director:Nicholas Stoller

    Writer:Francesca Delbanco

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    Director:Nicholas Stoller

    Writer:Francesca Delbanco