There are few gift-giving scenarios that induce quite the same level of cold sweat as having to select a present for someone you deeply respect but don’t know terribly well. That awkward territory where admiration meets uncertainty—where you want to make a good impression but lack the intimate knowledge of their preferences that makes gift selection feel secure. I’ve been there. Actually, I’m there more often than I’d like, given my tendency to develop intense professional admiration for people followed by a desperate desire to acknowledge them with the perfect gift.
Take my first meeting with Charlie’s parents, six months into our relationship. Charlie had spent weeks telling me how brilliant his father was—Cambridge-educated engineer, passionate jazz pianist, fluent in three languages. By the time we were due to visit, I’d built this man up in my head to mythical proportions. What on earth do you get for someone whose interests sound like the CV of a Renaissance man? I spent hours agonizing, discarding ideas, second-guessing myself. In the end, I panic-bought an expensive bottle of single malt whisky (despite having no confirmation he even liked whisky) and a book about the history of jazz (despite not knowing which volumes he already owned).
When we arrived, Charlie casually mentioned the gifts. His father looked genuinely touched but slightly puzzled. “That’s very kind,” he said, examining the whisky, “though I’m more of a gin man myself these days—doctor’s orders about the sugar.” The jazz book earned a polite nod. “I think I might have a similar one upstairs, but this looks fascinating too.” I wanted the floor to swallow me whole. Later, I discovered that what he really loved was growing chilli peppers on his kitchen windowsill and watching bad science fiction films—neither of which had featured in Charlie’s glowing descriptions or my imagined version of this intellectual titan.
That experience taught me a crucial lesson about gifting to people we admire but don’t know well: our admiration often creates a distorted image that has little to do with who they actually are as humans with ordinary preferences and quirks. We gift to the idea of them rather than the reality.
Since that mortifying evening (which Charlie still teases me about), I’ve developed a much more effective approach to these tricky gifting situations, whether they involve impressive new in-laws, professional mentors, or your child’s brilliant teacher who you desperately want to acknowledge properly at the end of term.
The first principle is deceptively simple: acknowledge the limits of your knowledge. This sounds obvious, but it’s psychologically difficult. When we admire someone, we want to demonstrate that we “get” them, that our admiration is based on genuine understanding. Accepting that we don’t actually know them well enough for a highly personalized gift can feel like admitting failure, but it’s actually the foundation of a much more authentic approach.
This principle saved me when I needed to find a gift for my new editor at British Celebrations. After she took a chance on me and my unconventional approach to gift writing, I was desperate to show my appreciation with the perfect present. I caught myself heading down a rabbit hole of investigation, trying to deduce her preferences from her sparse social media and offhand comments in meetings. Then I stopped and asked myself: what do I actually know for certain? I knew she was a brilliant editor who had shown faith in my work. I knew she loved independent magazines and good writing. And that was… pretty much it.
Rather than pretending to a level of personal knowledge I didn’t have, I embraced what our relationship actually was. I found a beautiful notebook from a small London stationer and wrote a heartfelt note about how much her editorial guidance had meant to me, citing specific examples of how she’d improved my work. The gift was a nod to our shared professional world, and the note acknowledged the actual basis of our connection. Her response was warm and genuine in a way I suspect wouldn’t have happened if I’d tried to guess at her personal preferences and gotten it wrong.
This leads to my second principle: focus on the authentic nature of your connection. With people we admire but don’t know well, there’s usually a specific context in which we know them—professional, academic, as an in-law, as a friend’s partner. Rather than trying to leap over this contextual relationship into fake intimacy, lean into the genuine connection you do have.
My friend Sophia got this exactly right when buying for her doctoral supervisor, whom she deeply respected but knew little about personally. Rather than guessing at his interests outside academia, she found a first-edition copy of an obscure philosophy paper they’d discussed in her first supervision—one that had fundamentally shaped her thinking. It acknowledged their academic relationship and showed she valued their intellectual exchanges without presuming greater familiarity.
The third principle is perhaps the most practical: when in doubt, consumables rarely miss the mark. Food and drink that can be shared or items that get used up don’t carry the same burden as permanent objects that might not match someone’s taste or needs. The key is to make these consumable gifts feel special and considered rather than generic.
When my literary agent Mira sold my book proposal after months of hard work, I wanted to thank her properly. Though we had a great professional relationship, I had little insight into her personal life or home decor preferences. I knew she was based in Edinburgh and had once mentioned enjoying the city’s independent shops. Rather than guessing at a permanent item she might not like, I researched small Edinburgh producers and created a hamper of artisanal items from her own city—small-batch gin, hand-made chocolates, locally roasted coffee, and Scottish shortbread from a tiny bakery. The gift acknowledged our professional victory while also recognizing her location and supporting local businesses she might already enjoy.
This approach has served me well with new in-laws (local specialties from where you live, presented as a cultural exchange rather than a presumption about their tastes), children’s teachers (consumables for the staff room with a specific note about their impact on your child), and new bosses (something related to a work achievement you’ve shared, rather than their personal life you know little about).
The fourth principle requires swallowing a bit of pride: it’s perfectly acceptable to do some diplomatic reconnaissance. There’s often someone in the admired person’s circle who knows them better than you do. Charlie would have been the obvious source of intelligence about his father’s actual interests, had I thought to press him for more mundane details rather than accepting his highlight reel of achievements.
When my cousin got engaged to a woman I’d only met twice but needed to buy a birthday gift for, I simply asked my cousin directly: “I’d love to get Sarah something she’d really like—what’s she into at the moment?” This isn’t cheating; it’s acknowledging the relationship as it actually is. His insider knowledge led me to a pottery workshop voucher that aligned with her newfound interest in ceramics—something I’d never have guessed from our brief meetings where we’d mostly discussed wedding plans.
The fifth principle is about presentation and explanation. When giving to someone you admire but don’t know intimately, how you present the gift and explain your thinking becomes especially important. A thoughtful note that acknowledges the nature of your connection and explains why you chose what you did transforms even a relatively simple gift into something more meaningful.
When I needed a thank-you gift for a senior editor who had given me valuable career advice during a brief mentoring session, I wasn’t presumptuous enough to think I knew her personal preferences after a single professional meeting. I chose a beautiful notebook (yes, I do give a lot of notebooks—occupational hazard for a writer) but made it special through my note, which detailed the specific advice she’d given that had helped me, how I’d implemented it, and the positive outcomes that had resulted. It showed I had genuinely valued and used her guidance, which was ultimately more meaningful than any object could have been.
The sixth principle is one I’ve adopted more recently: consider experience gifts that acknowledge shared interests without presuming to know their specific tastes. This has been particularly successful with my new father-in-law (yes, Charlie and I got married last year, and yes, his father and I now laugh about the whisky incident).
Rather than buying him objects, I’ve found that tickets to events related to interests I know he has—jazz performances, science lectures, botanical garden exhibitions for his chilli pepper obsession—work beautifully. These gifts acknowledge what I do know about him without pretending to an intimate knowledge of his preferences in physical items. They also create opportunities for shared experiences and conversation, deepening the relationship organically.
There’s another dimension to gifting to people we admire but don’t know well that deserves mention: the anxiety around gift value. There’s often concern about getting the financial calibration right—neither insultingly cheap nor uncomfortably extravagant. This is particularly acute in professional contexts, where power dynamics can make gift-giving fraught.
My approach here is to focus on thoughtfulness and specificity rather than monetary value. A modestly priced item that shows careful consideration of the relationship as it actually exists will almost always be better received than an expensive gift that feels generic or presumptuous.
When I was invited to speak at a conference organized by a writer I’d admired for years but never met, I wanted to bring a thank-you gift that acknowledged her influence on my work without seeming obsequious. Rather than something costly, I found a vintage postcard featuring the obscure literary location she’d written about in the article that had first introduced me to her work. I framed it simply and included a note explaining how that particular piece had shaped my thinking. It cost less than £15 all in, but the specificity made it meaningful in a way an expensive generic gift could never have been.
There’s one final principle I’ve come to value: sometimes, the most respectful gift is simply sincere words of appreciation. We often feel pressure to manifest our admiration in material form, but for many people—especially those in mentoring or teaching roles—knowing they’ve made a genuine impact is the most meaningful gift of all.
My most treasured professional “gift” was a detailed email from a reader explaining how my advice had helped her find the perfect present for her difficult-to-buy-for father, healing a long-standing tension in their relationship. No physical gift has ever meant more to me than that message. I try to remember this when I’m tempted to buy something for someone I admire primarily to ease my own anxiety about adequately expressing appreciation.
So if you’re currently sweating over what to get for your brilliant new boss, your child’s inspiring teacher, your partner’s parents, or anyone else you respect but don’t know well, take a breath. Accept the relationship as it actually is. Focus on your genuine connection. Consider consumables or experiences over objects that require intimate knowledge of taste. Do a bit of reconnaissance if appropriate. Write a meaningful note explaining your choice. And remember that sincere appreciation often matters more than the material gift itself.
Oh, and for what it’s worth, Charlie’s father now receives a different homemade chilli sauce from around the world every Christmas, and he tells me it’s the highlight of his gift-opening experience. Sometimes the perfect gift is hiding on a kitchen windowsill, not in a rare whisky or a jazz history book. And there’s no way to know that unless you’re willing to see the actual person behind the pedestal you’ve put them on.
Leave a Reply