Lori Gottlieb's life is ticking along nicely - until it isn't. Her boyfriend of many years leaves her, citing the fact that he doesn't want to be a father to her child as the reason. This all comes out of the blue, not least because he knew that she had a child when they began dating, and it is not something that he thought to bring up even as they made plans to get married. Gottlieb, a respected therapist, is plunged into depression. She knows the signs she understands all the emotions, because it is her own field, yet she cannot seem to talk herself out of the feeling that her life is unraveling around her.
Friends tell Gottlieb to see a therapist and talk to someone. She selects a therapist called Wendell, and for the first couple of sessions with him does nothing but sit on the couch in his office and sob, grieving over the loss of her boyfriend, her dream of marriage and happily ever after, and also the vision of herself as someone who knows exactly where her life is and where it is going. After she has stopped crying, and is ready to move forward in addressing the problem that exists in her emotional wellbeing, she is shocked to hear that Wendell believes her feelings are due to a lot more than sadness over the loss of her relationship and the violation in trust from her boyfriend.
Lori digresses, and starts to talk about patients of her own. John, for example, has two kids and is married, but doesn't think he has any problems. He doesn't really suffer fools gladly but thinks that if he didn't have to deal with so many fools then there would not be an issue in the first place. In John's world, everyone else is an idiot, but he is an accomplished, successful man. He is rude and obnoxious, even to Lori as his therapist, but with some work, she brings it out of him that he once lost a son, and that he has never properly grieved. His attitude and the problems that he is having in his marriage are just masking the underlying issue.
Gottlieb's next patient is Julie, a newly-wed, whose world is shattered when she finds out that she has cancer, and that it is inoperable and untreatable. Her feelings are complicated by the fact that she feels the weight of society's expectations of her weighing heavily.
Rita, almost seventy years old, is estranged from her adult children, which seems unfair because she was abused within her marriage and was never really the "bad guy". She never really lived up to her own expectations and is consequently very depressed about a life that has gone by without ever becoming what she felt it had the potential to.
After recounting the story of her patients, it is clear that Gottlieb is making the connection between her patients and herself; like them, she has unresolved, underlying issues that are being masked by a more present sadness to which she is attributing her depression. In Gottlieb's case, this is the fact that although she was interested in medical school, she never actually made the jump to go, leaving her preoccupied with feelings of having missed out on an opportunity that life was affording her.