Jack Grammar is in high school, and so unlucky in love that his two best friends go behind his back to design a personal ad for him: 'Jack Grammar is looking for a prom date - could it be you?' Natalie and Percy tell him that there have been tons of responses, and they design a plan...

Jack Grammar is in high school, and so unlucky in love that his two best friends go behind his back to design a personal ad for him: 'Jack Grammar is looking for a prom date - could it be you?' Natalie and Percy tell him that there have been tons of responses, and they design a plan. They will select 24 girls for him to spend time with in the seven days leading up to the prom, and he must select one of them to be his date for the night. But though Jack connects with many of the girls on his dates, he secretly finds himself falling for his friend, Natalie - and carrying on an e-mail relationship with the mysterious FancyPants. But will he ever be able to find the right girl?