Jeff Goldberg, a correspondent for The New Yorker, will never be accused of being naive. During his years reporting on Israel and the Middle East, he came into contact with all manner of politician and terrorist, providing detailed accounts of the region’s volatile ebb and flow and chronicling the myriad struggles among various religious, ethnic, and political groups seeking to reorder the contested landscape.

Even so, Goldberg has managed to retain an idealistic streak. Isn’t it possible, he wonders, for a Jew and a Muslim to be friends? But not just any Jew and Muslim — the Jew he chose to write about was an Israeli prison guard and the Muslim was his Palestinian prisoner. If you’re wondering about the Jew, yes, it’s Goldberg himself. Raised on Long Island, Goldberg made aliya and served as a military policeman before returning to the U.S.

The answer to the question Goldberg set out to explore is, not surprisingly, somewhat elusive. The mistrust, fear, and anger that so characterize the dealings between Israel and its neighbors play out, in part, in the relationship between Goldberg and Rafiq Hijazi, a member of Fatah; several years later they find themselves living near one another in Washington, DC. By then, Goldberg is establishing his career and Hijazi is a graduate student at American University.

Not all friendships come easy, but Goldberg does a good job of probing the complexities here. Rather than approach this clinically, he uses the memoir as a storytelling device. And so we’re given a window into his formative years, from his suburban childhood, which was sullied by kids who taunted him for being a Jew, through his coming-of-age camping experience in the Catskills, where he attended a Hashomer Hatzair camp, a socialist outback that stoked his budding Zionist urges.

Through it all, Goldberg spends a fair amount of time discussing his own psyche — the pushes and pulls that shaped his Jewish identity — before veering into his time as a kibbutznik and the moral vagaries of life as a shoter, or military cop, at the Ketziot prison. Of course, he also incorporates his various interactions with Palestinians, both as a prison guard and later as a journalist, as he attempts to fathom their withering views of Jews and Israel.

This is more than good reporting; it’s really an attempt to understand “the other.” To appreciate this great divide between Arab and Jew, Goldberg relates discussions with members of Fatah and Hamas, and he also recounts time spent in Afghanistan with Muslims who study Islam and train for jihad. Some conversations are predictable, especially the overtly political ones. More revealing are the talks he holds with devout Muslims as he attempts to decipher the Koran.

Meanwhile, Goldberg weaves in his growing number of encounters with Rafiq, first in prison, then Gaza, and later in Washington. That’s where he attempts to humanize and solidify their relationship. Their families eat dinner together. They meet for coffee at Starbucks. They talk about the stuff of life. Most of all, they dissect the Middle East, how each group views the other’s motives, behaviors, and demands. It’s a delicate dance, and each is often wary of the other.

In the end, Goldberg succeeds in using their balancing act as a way to examine the larger dilemma — Can Jews and Arabs live together as neighbors? Develop bonds instead of bombs? find meaning in getting to know one another? In the hands of an academic or policy wonk, such questions can sound brittle. A natural storyteller with a sharp eye for detail and an edgy wit, Goldberg has imbued these questions with an intimacy that implores a more personal discussion.

But can Goldberg and Rafiq actually become friends? You’ll have to read this book to find out. Bridging any divide is tricky, to say the least. Sometimes, the journey itself is the prize. The title of the book, of course, implies that both men have been prisoners, of one sort or another, and breaking those shackles can require a leap of faith. In his own astute and lyrical way, Goldberg does a provocative job of describing one man’s inquisitive and unrelenting attempt to make that leap.