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Movies like Dying Fall (2002)

Dying Fall tells the story of Ben, the estranged son of a well-to-do Boston family who has moved north to Halifax, Nova Scotia, to pursue his studies as a graduate student in music. Ben is stuck in an existential drift until he discovers that he has a potentially fatal aneurysm in his brain. This spurs him to seek out the one experience that he had until this point considered unimportant - trying to find a real connection with a woman, before it's too late.