Stella Payne, a very successful 40-year-old stockbroker, is a single parent raising her 11-year-old son Quincy in Marin County, California. Her friends and family chastise her for being without a relationship for too long.
Stella sends Quincy to his father's for two weeks and then, seeing an ad for Jamaican vacations, spontaneously calls her best friend from college, Delilah Abraham in New York City, to propose a visit. Her friend persuades her to go on a first-class vacation to Montego Bay, Jamaica.
As Stella soaks in the beauty of the island on her first morning there, she encounters a handsome young islander at breakfast. Winston Shakespeare is a chef's assistant and twenty years her junior, but very interested in her. He suggests they meet later at the hotel's disco pajama party. Winston's pursuit of Stella turns into a blossoming romance that is abruptly interrupted when a chef hires him as an assistant, which prevents her from seeing him for the rest of her trip. On her return to California, she discovers that a merger with another company has phased out her job.
Winston convinces Stella to visit Jamaica again, which she does with Quincy and his cousin. Delilah gives her a supportive call. Stella is taken to meet Winston's mother, who shames her as they are only a year different in age. This, along with a call from Delilah's oncologist, forces her to take personal inventory of her life.
Stella flies to New York to be with the dying Delilah. When removing cancer from one part of her body, her surgeon found a metastasis in her liver. The two friends are able to spend some time together in the hospital room before Delilah dies. Winston comes to New York for the funeral and then flies with Stella and her companions to California.
Upon arriving home, Stella's family, and even her ex, welcome Winston. After a short while, tensions rise between him and Stella. He thinks that she is ashamed to be seen with him and he finds her controlling, and she grows annoyed with his immaturity and youthful taste. Winston surprises her by fixing up her carpentry workshop.
Stella's old brokerage calls try to lure her back with the offer of a vice-president's position and a $275,000 salary, which she turns down to try to find her own firm. Amidst all her stress, Winston proposes. Stella temporises and dithers over her decision. After a week without an answer, Winston announces that he intends to go back to Jamaica and enroll in medical school, and takes a taxi to the airport. Stella intercepts him in the terminal and says yes to his proposal, having realized the need for balance between love and companionship and her responsibilities as a mother.
On Rotten Tomatoes, the film has an approval rating of 50% based on 50 reviews, with an average rating of 5.5/10. The website's critics consensus reads: "Angela Bassett gracefully breezes through a hot summer fling without much conflict or ado, leaving us wondering when -- or if -- she's ever getting that groove back."[7] On Metacritic, the film has a score of 56 out of 100, based on reviews from 23 critics, indicating "mixed or average reviews".[8] Audiences surveyed by CinemaScore gave the film a grade A−.[9]
Box office
In its opening weekend, Stella grossed $11,318,919, ranking #2 in the domestic box office behind Saving Private Ryan's fourth weekend.[10] The film would go on to gross $36,672,941 domestically and an additional $1,605,781 overseas for a worldwide total of $39,278,722, from an estimated $20 million budget.[2]