Wah Do Dem (2009)

Max lives in Brooklyn. He enjoys playing soccer, skateboarding, and drinking with his friends at local bars. Last summer he and his girlfriend, Willow, won a free cruise to Jamaica but two days before the trip she dumps him cold. When his friends flake, Max winds up alone on the high seas, navigating the crowds of gray-haired cruisers. Over the course of several days he flirts with the staff photographer, drinks cocktails with the boat's celebrity juggler and has several strange encounters with the only other loner.