• Air date: 05 Aug '25 10 episodes
      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.
  • List of Episodes (10)
    • 2. The Dinner Party

      05 Aug '25
      In an effort to get closer to Jenna, Sylvia and Charlie invite her and Will over for a couples dinner.
    • 3. The Bachelor Party

      12 Aug '25
      Sylvia and Will's college friend swings into town for the bachelor party. Sylvia helps Will to come to terms with his relationship.
    • 4. Fore!

      19 Aug '25
      Will advises Sylvia to go corporate. In San Diego, Will's plans with Jenna take an unexpected turn.
    • 5. Jeopardy

      26 Aug '25
      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!
    • 6. Road Trip

      02 Sep '25
      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.
    • 7. The Office Party

      09 Sep '25
      Will helps Sylvia throw a party for Charlie's law firm. Charlie makes an announcement.
    • 8. Young Darcy Mysteries

      16 Sep '25
      Sylvia gets hired to plan a major Hollywood party. Will finds an unlikely investor for his new bar. Charlie contemplates his professional future.
    • 9. Boundaries

      23 Sep '25
      To avoid dealing with Charlie, Sylvia invites herself along on Will and Katie's adventure to the LA River.
    • 10. Brett Coyote's Last Stand

      30 Sep '25
      Sylvia and Will's friendship hits a wall. Sylvia has a realization about her marriage. Will hears news about his bar.