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.
After a long rift in their friendship, Sylvia reunites with her old best friend, the newly divorced Will.
Episode 2. Gandalf the Lizard
2023-05-23 · 27 min
Will accompanies Sylvia to an open house. Sylvia helps Will sneak into his ex-wife's home to get the rest of his stuff and make a clean emotional break.
Episode 3. Partner's Retreat
2023-05-23 · 32 min
While Sylvia's husband attends a conference, she spends the day getting drunk with Will—who informs her about a development with his bar.
Episode 4. Divorce Party
2023-05-30 · 32 min
Sylvia throws a divorce party for Will to cheer him up, but it gets out of hand when his rowdy friends try to take control of the night.
Episode 5. My Wife's Boyfriend
2023-06-06 · 33 min
Unnerved by the closeness of Will's relationship with Sylvia, Charlie invites Will to join him and his coworkers at a baseball game.
Episode 6. The Big Two Six
2023-06-13 · 27 min
Will introduces Sylvia to his much younger girlfriend, Peyton—then gets upset when Sylvia hires her as a babysitter.
Episode 7. Let the River Run
2023-06-20 · 31 min
Sylvia struggles to keep up with the brutal pace at her new law firm. Will learns about Reggie and Andy's new plans.
Episode 8. San Diego
2023-06-27 · 29 min
Will and the guys take Sylvia on a business trip to San Diego. Charlie grows more suspicious about Sylvia and Will's relationship.
Episode 9. Slumber Party
2023-07-03 · 32 min
Frustrated by how much time Sylvia is spending with Will, Charlie crosses a line. Will confronts Reggie and Andy.
Episode 10. When Will Met Sylvia
2023-07-11 · 30 min
Tensions flare between Sylvia and Will at a housewarming party.
Season 2
10 episodes · 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.
Episode 1. The Engagement Party
2025-08-05 · 29 min
Sylvia and Will navigate the new boundaries of their friendship now that Will is engaged to Jenna.
Episode 2. The Dinner Party
2025-08-05 · 26 min
In an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner.
Episode 3. The Bachelor Party
2025-08-12 · 30 min
Sylvia and Will's college friend swings into town for the bachelor party. Sylvia helps Will to come to terms with his relationship.
Episode 4. Fore!
2025-08-19 · 32 min
Will advises Sylvia to go corporate. In San Diego, Will's plans with Jenna take an unexpected turn.
Episode 5. Jeopardy
2025-08-26 · 36 min
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!
Episode 6. Road Trip
2025-09-02 · 24 min
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.
Episode 7. The Office Party
2025-09-09 · 35 min
Will helps Sylvia throw a party for Charlie's law firm. Charlie makes an announcement.
Episode 8. Young Darcy Mysteries
2025-09-16 · 33 min
Sylvia gets hired to plan a major Hollywood party. Will finds an unlikely investor for his new bar. Charlie contemplates his professional future.
Episode 9. Boundaries
2025-09-23 · 30 min
To avoid dealing with Charlie, Sylvia invites herself along on Will and Katie's adventure to the LA River.
Episode 10. Brett Coyote's Last Stand
2025-09-30 · 40 min
Sylvia and Will's friendship hits a wall. Sylvia has a realization about her marriage. Will hears news about his bar.