Abbie Keller thought that Richard Bartholemew Benson the Third would be her forever. In their four years of dating, she never doubted that she wouldn't end up with his grandmother's engagement ring on her finger. Sure, she had to change a few things about herself to fit that mold, like dying her hair, dressing more conservatively, and finding golf enjoyable (honestly the most difficult of the changes), but she was sure that at the end of it all, it would be worth it. That is, until he leaves her crying outside her apartment wearing a Halloween costume, having broken it off with her because she's just not serious enough.

So she does what every girl does when she's broken up with: she calls her friends, gets drunk, dyes her hair, and formulates her plan for revenge. It just so happens that the universe supports her efforts and gives her the perfect match to prove to her ex that he made a huge mistake: his boss. But when the relationship starts to become something more than casual dating and Abbie sees that the tough New York lawyer has a soft side, will she be able to follow through with her plan of deceit?