In the Chicago area, public relations expert Olivia Kearns feels the world is changing so fast that she somehow has been left behind. She has noticed that her company seems more with it, but alas she is not, feeling like the poster girl for nerdette. Now she wants to cry because her parents are calling it quits. Liv is stuck making the apology calls after the cancellation of her parents? thirtieth anniversary due to their splitting. Amongst her calls, Liv speaks to her former boyfriend Nick Matheson. She realizes that he as a sports writer understands hip. So she turns to her Nick to teach her how to become outgoing and natural though not totally impulsive. Nick agrees to train Liv on how to live for the moment, but wants a favor back. He wants to interview a client of hers, who's such a hermit that he can't get to her without Liv. As he mentors her, they fall in love, but neither anticipated anything deep between the nerd in training and her teacher.