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Toby has always been unlucky with girls. Ever since getting stabbed in the throat after asking a girl out, Toby has resolved to learn everything he can about girls before meeting them. So he can become the man of their dreams. After faking yet another girlfriend, his mother takes matters into her own hands and signs him up with a dating coach. But Toby has finally found Phoebe. She's intelligent, enchanting and she's hot, everything Toby has been looking for. But this girl brings challenges that Toby hasn't had to face before including a boyfriend. Toby finds himself crossing lines he never thought he'd cross. Then there's the problem of how to keep her, without her finding out that he knows everything about her. How far would you go for a crush?