Annie Bailey’s not a tomboy. She's not a slut either. But when it comes to dating, she acts like a guy. After the end of a codependent relationship, Annie develops a number of unemotional male-like rules to govern her interactions with men. She masters the wingman move, categorizes guys into those you sleep with and those you date, and does “the fade” when she’s not interested. Annie hides behind the facade of her dating dogma, preferring to analyze men rather than her own life goals. She refuses to act like a “silly woman,” believing she can convince herself to like her boring job, remain free from heartache, and prove that women don’t have to let emotion overcome logic. As Annie approaches her 27th birthday, and as her friends bypass her in their careers and relationships, it becomes more and more difficult for this wise-cracking, quirky girl to leave her own life unexamined. Will Annie mature into the woman she’s afraid to become, or will she remain fixated on giving men a dose of their own dating medicine?