Hollis Shaw’s life seems picture-perfect. She’s the creator of the popular food blog Hungry with Hollis and is married to Matthew, a dreamy heart surgeon. But after she and Matthew get into a heated argument one snowy morning, he leaves for the airport and is killed in a car accident. The cracks in Hollis’s perfect life—her strained marriage and her complicated relationship with her daughter, Caroline—grow deeper.
So when Hollis hears about something called a “Five-Star Weekend”—one woman organizes a trip for her best friend from each phase of her life: her teenage years, her twenties, her thirties, and midlife—she decides to host her own Five-Star Weekend on Nantucket. But the weekend doesn’t turn out to be a joyful Hallmark movie.
The husband of Hollis’s childhood friend Tatum arranges for Hollis’s first love, Jack Finigan, to spend time with them, stirring up old feelings. Meanwhile, Tatum is forced to play nice with abrasive and elitist Dru-Ann, Hollis’s best friend from UNC Chapel Hill. Dru-Ann’s career as a prominent Chicago sports agent is on the line after her comments about a client’s mental health issues are misconstrued online. Brooke, Hollis’s friend from their thirties, has just discovered that her husband is having an inappropriate relationship with a woman at work. Again! And then there’s Gigi, a stranger to everyone (including Hollis) who reached out to Hollis through her blog. Gigi embodies an unusual grace and, as it happens, has many secrets.