Demolition Davis (Jake Gyllenhaal) is a successful private equity partner who struggles after losing his wife in a tragic car accident. Despite pressure from his father-in-law, Phil (Chris Cooper), to pull himself together, Davis continues to unravel. What starts as a complaint letter to a vending machine company turns into a series of confessional letters revealing startling personal admissions. Davis’ letters catch the attention of customer service representative, Karen (Naomi Watts), and amidst their own emotional and financial burdens, the two form an unlikely connection. With the help of Karen and her son Chris (Judah Lewis), Davis begins to rebuild, starting with demolishing the life he once knew.