Jesse (Tim Daly) has never had a problem finding a girlfriend. It's maintaining the relationship that's his issue. When an ex-girlfriend of his dies, Jesse impulsively asks his most recent fling, Hannah (Olivia d'Abo), to marry him -- a proposal she quickly turns down. Left confused by the rejection and his dating history, Jesse decides to seek out his former loves for answers on why the relationships ended. While traveling to the funeral, Jesse has quite a few detours to make along the way.