Humorous novel about a man in a religious order who is sent into the outside world by his order, and has his worldview changed by his experiences

Question

Today, at church, the priest was discussing the Sacrament of Reconciliation, both commenting on how even priests and nuns go to Confession regularly and on how, as a priest, he's noticed that people tend to come in with the same sins week after week, so he sometimes wondered how many of us truly examine ourselves and try to improve yourselves (this being in light of the Gospel reading about the three servants entrusted with their master's wealth, and what they did with them).

I think I read this in the mid 1990s. I remember the author had several books, all in a dark humor category, but I can't recall his name, although I remember the concept of religious orders popping up in another series. This book was a standalone. The main character was an adult male who is a member of a religious (Catholic, I'm pretty sure) order that sequestered themselves away from the world in order to pursue a life of quiet contemplation and prayer. As I recall it, he was trying to be a good member of the order, but didn't quite feel like he reached the right level of piety despite his attempts. I recall that he commented on how they were expected to go to Confession regularly, and were not allowed to leave without confessing something, which led to him making up sins, and then feeling guilty about lying, and confessing those lies. What kicked off the plot was that something is going on with the order where they needed to send someone out into the world to resolve a matter, I think maybe involving some aspect of land ownership where the monastery is? The protagonist is chosen to go into the outside world, which is set somewhere in the 1970s to 1990s, I think (nothing stuck out as being particularly "old" sounding, but I don't remember cell phones coming up, or the Internet).

After that, I don't remember much of the rest of the plot. It's largely humor about the protagonist being a fish out of water, dealing with the sinful regular world, and when he returns to the monastery (I think successful in his endeavor), he at first thinks the outside world has corrupted him, but he instead realizes that he joined the monastery not out of devotion, but as a way to escape his former life, and that that is the wrong motivation. I do remember that he takes a trip on an airplane and experiences the wonders of miniature liquor bottles (I want to say they were complimentary, which would probably date this story as being further in the past when there wasn't as much cost-cutting and flying was seen as a luxury experience), and I think he comes home with a suitcase full of them, many of them empty because he just likes the way they clink together.

It was a hardback, probably in the 200-300 page range, and when I read it, it looked at least a few years old. The pages had some wear and were starting to darken with age, but didn't seem yellow and brittle.

Answer 1

In the process of writing the question, I remembered the author, Donald E. Westlake (I went through a bunch of his Dortmunder books, of which our local library had a fair collection), and a search for donald westlake religious brother led me to Brothers Keepers.

When the order's lease on the Park Avenue monastery expires, sixteen monks face a greedy real-estate mogul, and Brother Benedict falls in love with the mogul's daughter.

One of the reviews mentions the confession scene and better describes the plot:

Starting in inimitable Westlake style with a confession scene that had me bursting out laughing,this newly repackaged and republished copy of ‘Brothers Keepers’ is a pure delight to the very last page.

It captures a time in the mid 70’s that most of us would find hard to recall,especially not this reviewer, ahem, who is FAR too young to remember and heard about it from her grandparents, and that in and of itself is part of the book’s charm. This tiny patch of land, this monastery is the last bastion on Park Avenue against the encroaching tide of skyscrapers.

Brother Benedict , a 34 year old Christinian monk who has lived in the monastery for the past 10 years after converting to Catholicism to win the heart of a girl who ran off and left him anyway, prefers life inside the cloisters. It’s quiet, straight forward and the routine gives a lot of comfort to a man at odds with modern 20th Century life in New York.

He accidentally comes across the plans to demolish several buildings, including theirs, in an architectural think piece published in the Sunday Times, his weekly indulgence. The journalist is outraged at the encroachment of modern building and the underhand methods used to acquire either land,buildings or both.The monastery has stood on leased land, for 2 centuries, passing from the monastery founder to the Flattery family after the original 99 year lease expired.

Now 16 world weary, but also unworldy, monks have the fight of their lives on their hands. It’s them versus the Flattery’s as they battle to preserve their way of life in a world that no longer recognises the rights of this minority religious order.