A longtime group of friends reunite and travel to Napa Valley, California, to celebrate Rebecca (Rachel Dratch)'s fiftieth birthday. However, it doesn't take long for their issues to surface and their friendships to be tested. Abby (Amy Poehler) attempts to keep a rigid schedule, Rebecca is seemingly not excited to be turning fifty and is in denial about the state of her marriage, Naomi (Maya Rudolph) is hesitant to call her doctor about a medical diagnosis, Catherine (Ana Gasteyer) feels like the others leave her out, Jenny (Emily Spivey) is indecisive and miserable, and Val (Paula Pell) just wants to find love. What follows is a series of misadventures as the women try to get through the weekend and introspect about themselves and their relationships.
Tina Fey and Jason Schwartzman also have roles as Tammy, the guesthouse owner, and Devon, the housekeeper/chef/driver, respectively. The film was directed by Amy Poehler in her feature directorial debut. It was released on Netflix on May 10, 2019.
- Age-Gap Romance: The middle-aged Val has a brief flirtation with Jade, a young artist.
- All Part of the Show: The group gets into a fight at Jade's art show, but they are able to pass it off as all part of the exhibit.
- As Herself: Brené Brown appears as herself.
- Control Freak: Abby, who put together a very detailed itinerary and tries to follow it to the letter, which eventually gets on the others' nerves. It is later revealed that this is because she just lost her job and is trying to find something that she's in control of.
- The Friend Nobody Likes: Played With. Catherine feels like the others exclude her, and distances herself somewhat from them as a result by throwing herself into her work. The others point out that this only increases the feeling of being left out.
- The One Guy: Devon is the only male character with a major role.
- One-Track-Minded Artist: Jade's art is all paintings of Fran Drescher in The Nanny. The main characters are confused by it, but the other guests at the art show (Californian hipsters) appear to consider it high art.Jade: It's really a lettera d'amore to The Nanny. But, more importantly, it's a reaction to all of our experiences surrounding The Nanny.
- The Topic of Cancer: Naomi is terrified of calling her doctor to check for her breast cancer test results.
- True Art Is Incomprehensible: In-Universe, the characters can't understand why Jade's collection of Fran Drescher portraits mean, but the Californian hipsters around them consider it high art.
- Wine Is Classy: The ladies are taking a wine tour throughout Napa Valley. None of them really have the patience for the spiffy Sommelier Speak.
- Workaholic: Catherine is always on her phone about a lucrative job offer, even after the others tell her to disconnect.