Charlie, a talented sailor, is deeply affected by a tragic car accident that claims the life of his younger brother, Sam. Struggling to cope with the loss, Charlie takes a job at the cemetery where Sam is buried, retreating from the world and distancing himself from his dreams of attending Stanford University. He soon discovers that he can communicate with Sam's spirit, and they make a pact to meet every evening to play catch and talk. This peculiar connection to the afterlife keeps Charlie bound to his grief, anchoring him in the past while the world moves on without him.

Years pass, and Charlie encounters Tess, a former high school classmate and professional sailor preparing for a solo voyage around the world. As they grow closer, Charlie begins to find himself torn between his promise to Sam and his growing feelings for Tess. This budding relationship challenges Charlie to reconsider his attachment to the past and contemplate a future where he might find happiness again.