Jack Darcy appears to have it all--a rich surgeon from an influential family of doctors and researchers. Oh and he is drop dead gorgeous with high end condo. But yet, Jack is incredibly single. Without a single prospect. It doesn't help that he keeps screwing up every first date. How was he supposed to know that his date was NOT pregnant?! Or that he would blank out and forget the name of his date. It's not his fault that he ordered a meat lover's pizza while on a date with a vegan. Why would a vegan agree to a pizza date? Jack is awkward around women with the exception of his best friend, Allie Jenkins. Allie and Jack have known each other since birth. Ok, more like a few weeks later. But still. Their parents work together and are friends. Jack is a few years older than Allie but that doesn't stop Jack from dreaming about her. He hopes that she can help him. More importantly, he hopes that all these lessons lead him to her heart. He thought that would be crystal clear to Allie after a disastrous double date where their dates ended up making out in the hallway. But instead that made her even more determined. He was determined to show her how he felt.