I read this on the recommendation of a fellow A.P. English teacher who likened it to a modern-day version of Sherwood Anderson's Winesburg, Ohio. I remember enjoying Anderson back in college, so I figured I'd give this book a whirl. It did NOT disappoint!
Strout's book is a collection of basically thirteen short stories, all pertaining to various residents of the small town of Crosby, Maine and all connected somehow by the titular character. Olive is a retired middle-school mathematics teacher, a big woman who loves her Dunkin' Donuts and speaking her mind plainly, and throughout the collection of stories we see Olive and a cast of others going about the activities of life: attending weddings and funerals, working unfulfilling jobs, engaging with soul mates, fretting over in-laws, fending regrets. Olive is the unifying element within each story, since most of the stories focus on other characters or families ... but by book's end you get a poignant portrait of this woman as she -- like all of us -- attempts to make sense of this thing called Life.
Olive Kitteridge is in beautifully written prose, yet I cannot help but wonder if a high school kid will really "get" what makes these characters work. In much the same way I tried to teach Dickens's A Christmas Carol a few years ago and learned, by the end, that the reason why I was the only one with tears in his eyes was because I, unlike the average seventeen-year-old, had actually lived life long enough to have regrets -- in this way, I doubt my students will really understand what makes these characters work. Nevertheless, each story is an outstanding exercise in characterization, so it's definitely worth a try.
Enjoy reading Olive Kitteridge!