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 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.