Gifts for Hard to Buy For People: The Art of Thoughtful Selection

Every family has one. Every friend group contains at least two. The person who, when asked what they want, shrugs and says “nothing, really” or worse, “I don't know.”

These individuals have earned various labels: picky, particular, impossible to shop for. Winston would suggest a different framing. Such people are not impossible to delight—they are simply impossible to satisfy with obvious choices.

Why Some People Seem Difficult

The “hard to buy for” designation typically applies to people who share certain characteristics:

They have specific tastes. General categories do not apply. They do not simply “like books”—they read particular authors, in particular editions, and already own the obvious choices.

They value quality over novelty. A mediocre version of something they might want disappoints more than no gift at all. They would rather have nothing than something that misses the mark.

They acquire what they want. Unlike those who maintain wish lists of deferred desires, these individuals tend to purchase items that genuinely interest them when the interest arises.

They feel genuinely uncomfortable receiving gifts. For some, the obligation implied by gift-receiving creates anxiety that overshadows any pleasure the gift might bring.

Understanding which category applies to your particular difficult recipient helps considerably in addressing the challenge.

Strategies by Type

For the Person with Specific Tastes

The temptation is to stay within their known interests but choose something generic—a book by an author they have mentioned, a wine from a region they favour. This approach rarely succeeds.

Instead, go deeper rather than broader. If they love a particular author, find an unusual edition, a collection of letters, a biography, or an item connected to that author's world. If they favour a certain wine region, find the smallest producer making the most distinctive wine—something they could not easily encounter themselves.

The goal is not to satisfy their stated interest but to surprise them within it. Show them something they did not know existed in a domain they thought they knew completely.

For the Quality-Focused Individual

These recipients have rejected so many gifts because the gifts failed to meet their standards. The solution is not to find something so expensive it must be good—quality and price correlate imperfectly.

Instead, find items where the maker's obsession matches the recipient's standards. Artisans who refuse to compromise, small producers who could increase volume but choose not to, creators who have spent decades perfecting a single product. Such items carry their own evidence of quality; the recipient recognises a kindred spirit.

For the Person Who Already Has What They Want

This person does not maintain desire for material goods because they have learned to satisfy such desires immediately. The opportunity here is to offer something they could not have acquired themselves.

Experiences over objects, certainly, but not generic experiences. A cooking lesson with a specific chef whose work they admire. Access to a private collection they would never have known to request. An introduction to a world adjacent to their interests but previously unknown.

Alternatively, offer something that requires external selection. They know what they want; you know something about what they might want that they do not know themselves. A carefully curated selection, chosen by someone who observes them carefully, often succeeds precisely because they would never have chosen it.

For the Gift-Averse

Some people genuinely dislike receiving gifts. The obligation to respond appropriately, to perform gratitude, to find space for another object—these create genuine discomfort that outweighs the gift's pleasure.

For such individuals, consider gifts that eliminate the performance aspect: something consumable that requires no permanent home, something that arrives when they are not present to receive it, something presented with explicit permission to discard if unsuitable.

Or consider making the gift about relieving a burden rather than adding to their possessions: a service that handles something tedious, a membership that simplifies something complicated, an arrangement that makes their life slightly easier without requiring their attention.

The Observation Approach

Regardless of which type of difficult recipient you face, the most reliable approach involves observation rather than inquiry.

Asking “what do you want?” yields nothing useful from these individuals. They either do not know, do not wish to say, or do not believe you will find something adequate.

Instead, observe. What do they notice? What comments do they make in passing? What do they reach for, examine, then put back? What aspects of others' possessions draw their attention?

These observations, accumulated over time, reveal genuine preferences more reliably than any direct question. The difficult recipient often does not know what they want—but they know it when they see it, and they reveal this knowledge constantly in small ways.

When in Doubt

If observation fails and strategies founder, Winston suggests this: find someone whose judgment you trust—whose taste seems likely to align with your difficult recipient—and delegate the selection.

This is not laziness but wisdom. A fresh perspective, combined with genuine skill at selection, often succeeds where personal knowledge fails. The person who knows the recipient too well may overlook possibilities that an informed outsider would immediately see.

The key is choosing your delegate carefully. Not a generic service that categorises people by demographics, but someone or something that takes time to understand the specific individual you are trying to delight.

A Closing Thought

The “hard to buy for” person is difficult precisely because they cannot be satisfied with obvious choices. This difficulty is, paradoxically, an opportunity.

Easy-to-please recipients accept almost anything graciously. Difficult recipients, when genuinely delighted, respond with memorable surprise. Their standards, so frustrating in the usual gift-giving context, make success all the more satisfying when achieved.

Winston finds such challenges rather the point.

For those facing a difficult recipient and seeking assistance, Winston remains available. Some puzzles benefit from collaborative solving.