Originally published in 2004 by Knopf Canada, it was the winner of the Governor General's Award for English Fiction, and was nominated for the Giller Prize. It spent over a year on the Canadian bestseller lists. East Village, the town in the novel, is generally considered to be a fictionalized version of Toews' hometown of Steinbach, Manitoba.

The novel is told as a memoir of the fictitious character Nomi Nickel, a teenage girl embarrassed by her heritage who longs to escape to New York City to hang out with Lou Reed. At the end of the book it is revealed that she has addressed the memoir to Mr Quiring, one of her school teachers.

A Complicated Kindness was chosen for inclusion in Canada Reads 2006, where it was championed by singer-songwriter, poet and publisher John K. Samson. It won the competition.

The novel is told in the style of a memoir and is not fully chronological; therefore there is no classical plot line. The most present-day events detail the involvement of the main character, Nomi, with Travis, whereas she also explores her past and how her family came to be so fragmented.

It is revealed that Nomi's sister, Tash, was excommunicated and left town during her late teens, with her boyfriend, Ian. Tash had become an atheist and her rebellious spirit was not satisfied with the limits of the Mennonite community. Seven weeks later, Trudie, Nomi and Tash's mother is also excommunicated and leaves town to spare Ray, her husband and the girl's father, the agony of choosing between her and the church. Nomi speculates that Trudie left her with Ray because Ray needs Nomi more than Trudie does. She also speculates that Trudie knew Ray would not be able to choose between her (Trudie) and the church and therefore she left to make it simpler for him.

With Travis, Nomi becomes more rebellious; she spends most of her time trying to get high and eventually begins to take oral contraceptives and loses her virginity. She stops going to school and church. At the end of the novel, Nomi is excommunicated for various reasons, and Ray leaves town because he realizes that Nomi wouldn't have the heart to leave him, and therefore must leave so that Nomi would be free to do the same. It can also be interpreted as a suicide on the part of Ray.