Choosing a book for someone whose taste you don't know
You drew a name in a book exchange and you know two things about the person: where they sit, and that they once mentioned a holiday in Portugal.
This feels like an impossible brief. It is not — it is a category problem, and the categories are well mapped.
Ask one question, not about books
“What do you do on a Sunday?” tells you more than “what do you read?” ever will.
People answer the reading question with the books they think they should be reading. They answer the Sunday question honestly, and a Sunday spent cooking, walking, in a museum or dismantling a bicycle each points straight at a shelf.
If you cannot ask them, ask somebody who sits near them, or read what they have said about themselves anywhere you already have access to. Ten minutes is enough.
Four categories that almost always land
Short stories. The most underrated gift in the shop. No commitment, no obligation to finish, and a bad story costs the reader twenty minutes rather than a fortnight. Excellent for anybody who says they do not have time to read.
Non-fiction about a thing they visibly like. The book about bread for the person who bakes, about birds for the person who walks, about a city for the person who is moving there. The subject does the work, and you do not have to be right about their taste in prose.
A reissued classic in a beautiful edition. They have probably not read it, they will not be offended, and the object itself is a gift. This is the safest choice in the shop and it is safe for a reason.
Illustrated or photographic books. Almost no risk. They get looked at rather than read, they survive on a table for years, and they work for people who genuinely do not read much.
Four that almost never do
The bestseller everybody is talking about. Half the group has already read it, and the other half decided not to. It is the one book you can be confident is not a discovery.
Self-help, in any form. It reads as a diagnosis, even when it is not meant that way. The same is true of anything about productivity, decluttering or health.
A 900-page novel. It is a commitment, not a present. Nobody wants to owe somebody three weeks.
Book four of anything. Obvious once said, and it still happens every year.
Use the shop, not the search box
A bookshop is a better tool for this than any website, because the constraint of what is physically on the table produces choices an algorithm never surfaces. And staff in a good shop answer the question “I need a book for somebody who likes cooking and is quite funny” better than any recommendation engine.
Second-hand shops are better still if the exchange allows them — and a book swap should say plainly whether it does, because half a group will otherwise assume new-only.
The part that actually matters
Write inside the cover. One or two sentences on why you chose it, unsigned if the exchange is secret.
A book that arrives with a reason is a recommendation. The same book with no note is an object somebody bought. It is the cheapest possible upgrade to a gift, and it takes a minute.
If you are truly stuck
Buy the book you would want somebody to give you, and say that in the note: that you did not know them well, that this one mattered to you, and that you were curious what they would make of it.
That is a real gift — the honest kind — and it is far better received than a safe choice made without conviction.