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’ 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 20s, her 30s and midlife --- she decides to host her own Five-Star Weekend. But the weekend doesn’t turn out to be a joyful Hallmark movie.