A week before Joey is set to marry his fiancé Luca, he and his best friend Kris set off to celebrate his bachelor weekend. Joey and Kris return to the town of Beacon Point, the place they called home during their college years. Kris planned a weekend filled with beach adventures, hitting up old haunts, and celebrating with old friends. Their plans are thwarted when Joey and Kris stumble into a shop and meet "The Woman," who claims she has the ability to show Joey how any of his prior relationships could have turned out. Joey is soon thrust into the past, reliving former love and how different life could have been. Will Joey realize his life is better off with Luca, or will he be caught up in one of the what-ifs?