'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.