Event planner Pepper Pomeroy is making the most of her current unemployment by arranging a surprise for her sister, Felicity. Warren, Felicity's boyfriend, plans to lure his lovely lady into a private jet, propose, and whisk her away on a romantic vacation. He just needs Pepper to handle all the fine details in order to make it the perfect proposaland it is. Everything goes so well when Warren pops the question that he suggests Pepper do this sort of thing professionally.