A mushroom trip brings free-spirited Elliott face-to-face with her 39-year-old self. But when Elliott's "old ass" delivers warnings to her younger self, Elliott realizes she has to rethink everything about her family, life and love.

Davis (Jake Gyllenhaal), a successful investment banker, struggles after losing his wife in a tragic car crash. Despite pressure from his father-in-law, Phil (Chris Cooper), to pull it together, Davis continues to unravel. What starts as a complaint letter to a vending machine company turns into a series of letters revealing startling personal admissions. Davis' letters catch the attention of customer service rep, Karen (Naomi Watts), and, amidst emotional and financial burdens of her own, the two form an unlikely connection. With the help of Karen and her son Chris (Judah Lewis), Davis starts to rebuild, beginning with the demolition of the life he once knew.