The quartet in this film is Susan Sarandon as Lou, an uptight, humorless cat lady and cardiac surgeon; Bette Midler as Marilyn, a wealthy recent widow who impulsively decided to get married again two months after the death of her husband of 48 years; Megan Mullally as Alice, a popular singer who is perpetually tipsy, high on drugs, or having sex with randos, sometimes all at once; and Sheryl Lee Ralph as Kitty, a kind-hearted weed grower and mother of an adult daughter who has suddenly become rigidly religious. You can glimpse Midler’s real-life daughter, Sophie von Haselberg, playing Marilyn’s daughter early in the film.
Marilyn is staying in a gorgeous mansion in Key West, where Ernest Hemingway lived when he wrote two of his books, which we are told so often they could be getting paid by the mention. She invites Kitty and Alice to her wedding but does not invite Lou because they have been estranged for years. So Kitty and Alice tell Lou the kind of preposterous lie that only works in painfully contrived screenplays: they don’t mention Marilyn. They just say she has won a six-toed cat from the Hemingway House.
When Lou finds out she’s been tricked, she agrees to stay. However, she is clearly still in pain over the sense of betrayal by Marilyn, for reasons telegraphed so unmistakably from her arrival in Key West that the ultimate reveal carries no weight. Throughout the trip, she keeps running into a group of 20-somethings she met on the plane and accidentally becomes their badass ideal.
Marilyn is so excited about her over-the-top wedding plans she barely notices that her friends think she is over the top. For another one of those reasons that only works in painfully contrived screenplays, she does not introduce her fiancé to her friends until the night before the wedding so there can be a very predictable twist. But the four are too busy having wacky adventures. Lou uses a Kegel (pelvic floor) exercise ball Marilyn gave her as a slingshot to take out a bicycle thief! Lou accidentally unties the rope to the parasail because she is hallucinating! Yes, it is supposed to be a funny prank that Lou’s closest friends dose her with weed without telling her. Another intended-to-be hilarious scene takes place in a strip club, where a star performer connected to one of the women is recognized when she sees the birthmark on his bare butt while he is grinding on the bride-to-be.