Dave, a charmingly irresponsible sales rep who cycles through dates and jobs like his breakfast cereals, faces a family ultimatum: find a serious partner before his brother's wedding or get cut off. Across town, Rebecca, a sweet but stubbornly idealistic romantic, receives a similar threat from her best friend. Forced to collaborate on a potentially disastrous pre-wedding event, this unlikely duo must navigate the treacherous waters of the dating scene to find appropriate dates. But as they bicker and bond over disastrous dates and wedding mishaps, they might just discover that the perfect match was right in front of them all along.