Law student Brooke Sherman leads an enviable life, with an impressive education, a prestigious internship, and an ambitious boyfriend who any girl on campus would love to date. But one phone call shatters everything: her father, the optimistic man who insists on buying lottery tickets and dreaming big, has terminal cancer. Desperate to get home and predictably unable to rely on her boyfriend, Brooke finds an unlikely hero in the form of her classmate.

Jason Ramsey has had a crush on his study partner Brooke for months, but he'd never encroach on someone else's girlfriend—even if the guy doesn't treat her the way she deserves. But when he learns of Brooke's father's diagnosis, Jason steps up to help however he can. In the weeks and months following, Jason is Brooke's rock, and after Brooke's breakup, Jason becomes much more than just a friend. But even as they plan for a future together, things get complicated: Brooke's father had a dying wish, that his daughter buy one last lottery ticket. She never dreamed that fulfilling that wish would jeopardize a future with the man she loves.