‘Why is it taking us so long to settle down and find ‘the One’?’ Jack Ridley, a mid-30-something former White House staff, former lawyer, former failed screenwriter, and wannabe former teacher, is struggling not only to write a book to be published, but to find a partner and direction in life. Suffering an extended post-adolescence, Jack falls into interviewing groups of women as a way not only to find his book but also the angle allow him to meet great women the way he used to. In his first interview he meets Alex, a beautiful, force-of-nature personality who falls for who she believes Jack to be, and seizes on filming the discussions as the perfect antidote for reality television. In the process, she hijacks his project and without realizing it causes him to face ghosts of relationships past. Through a series of revealing discussions, Jack finds himself coming uncomfortably closer to the reality he’s denied: experiences that have caused him to hide his true self and rely on ‘angles’ to meet women. Alex misinterprets Jack’s reactions to women’s stories, believing him to be a better listener than he himself believes. The more she tells Jack how different he is from other men and how attractive that is to her, the more Jack is tortured by the prospect of Alex finding out the truth he believes about himself before he can find the courage to become the man he needs to be.