Burke Ryan (AARON ECKHART) is a widower of three years who accidentally parlayed his grief into a successful career as a grief counselor and motivational speaker. In fact, he's so good at what he does, his manager, Lane Marshall (DAN FOGLER), is on the verge of landing a potentially lucrative business deal to market Burke's work and brand.
Yet, Burke isn't happy that meeting or his next seminar will take place in Seattle. After all, that's where he and his wife once lived, and he's had no contact with her parents, including her ex-Marine dad Silver (MARTIN SHEEN), since a car accident took her life. Even so, Burke is committed to helping his clients, such as Walter (JOHN CARROLL LYNCH), a former contractor whose 12-year-old son died in a past accident.
Knowing that Burke is solely focused on his work, Lane encourages him to get out there and live. Taking that advice to heart, Burke decides to approach Eloise Chandler (JENNIFER ANISTON) who runs a florist shop with her lone employee, Marty (JUDY GREER), and delivers arrangements to the hotel where Burke's A-Okay seminar is being held.
As they get to awkwardly know each other, Eloise eventually realizes that while Burke is successful at helping others, he's never fully helped himself. From that point on, she tries to convince him to take some of his own medicine and advice so that he can finally move on with his life.