We’ve all got one. That person who makes you break out in a cold sweat when their birthday rolls around or their name gets pulled in the office Secret Santa. You know exactly who I’m talking about – the impossible-to-shop-for relative, the picky friend with specific tastes, or maybe the in-law who seems to have everything and likes… well, you’re not entirely sure what they like.
I used to have a system for these people. It was called avoidance. Gift cards, generic candles, or in truly desperate situations, a “charitable donation made in your name” (which, let’s be honest, sometimes meant I panicked and had nothing else to give).
My gift-dodging strategy fell apart spectacularly about four years ago with my father-in-law, Richard. Richard is lovely but notoriously difficult to buy for. He’s the kind of man who buys himself whatever he wants when he wants it, maintains exactly six interests that never change, and responds to direct questions about gift preferences with “Oh, I don’t need anything, don’t trouble yourself.”
For his 65th birthday, Jake and I had settled on our usual – a nice bottle of Scotch (safe, predictable) – when my sister-in-law casually mentioned she’d gotten him a personalized leather case for his favorite fishing lures with his initials embossed on it. It was thoughtful, personal, and played perfectly into one of his core interests. I felt that particular sting of gift inadequacy that I normally only experience when scrolling through elaborate Pinterest birthday parties.
“We can still get something else,” Jake suggested, clearly sensing my distress. “Dad won’t mind if we’re a little late with his gift.”
“The party is tomorrow,” I reminded him. “And your sister is apparently gunning for ‘favorite child’ status with her perfect gift that probably took weeks to order.” I was being dramatic, but you know how it is with siblings and in-law dynamics.
That night, unable to sleep, I found myself digging through old photos from family fishing trips, remembering how Richard always told the same three fishing stories after a couple of Scotches. There was one about “the monster pike that got away” at his favorite lake in Minnesota when he was twelve. He’d described that lake and that moment so many times I could practically see it.
At 2 AM, I had a ridiculous idea. By 7 AM, I was at an art supply store buying materials I hadn’t touched since college. By that afternoon, I’d painted a small watercolor of that Minnesota lake, complete with a monstrous pike jumping out of the water. I framed it in a simple wooden frame with a hand-lettered caption: “The One That Got Away – Lake Vermilion, 1970.”
It wasn’t perfect – my artistic skills are mediocre at best – but it was specific to him. When Richard opened it the next day, he stared at it for so long I thought maybe I’d completely missed the mark. Then I noticed he was blinking rather rapidly.
“You remembered that old story,” he said quietly. “Nobody ever remembers that story.” (Not true – everyone remembered it because he told it at every family gathering, but this wasn’t the moment to point that out).
That painting now hangs in his study. The bottle of Scotch was appreciated and promptly consumed, but the painting sparked a connection. It was the first time I’d gotten beyond the surface with Richard, and it taught me something important: Sometimes the most challenging people to buy for are actually giving us the clearest blueprints for meaningful gifts. We just have to listen differently.
Since then, I’ve made it my mission to crack the code of gifting for difficult people. Not because I’m some sort of gift saint (trust me, I’ve given plenty of terrible presents in my day), but because I’ve seen how the right gift can build bridges with the people we find most challenging to connect with.
Here’s what I’ve learned about approaching these gift conundrums:
First off, difficult gift recipients usually fall into a few distinct categories. There’s the “literally has everything” person (my mother-in-law who buys herself every kitchen gadget the moment it hits the market). The “extremely particular” person (my friend Denise who returns 80% of what she receives). The “I don’t want anything, don’t make a fuss” minimalist (my brother who gives away most material possessions). And finally, the person where the relationship itself is complicated (like my aunt Susan, with whom conversations are a political minefield).
For the person who has everything, I’ve found the sweet spot lies in consumables or experiences. My mother-in-law may own every kitchen gadget, but she won’t say no to a basket of specialty ingredients from cultures she’s less familiar with. Last year, I put together a “Mediterranean exploration” basket with olive oils from small family producers in different regions, along with a beautiful hand-painted olive wood spoon. She texted me photos of every dish she made with those ingredients for months after.
The extremely particular person requires reconnaissance. My friend Denise is notoriously picky, but I realized she never returns items from one specific home goods store. Why? Their return policy is a nightmare, and she can’t be bothered with the hassle. Rather than seeing this as a challenge, I now see it as a helpful boundary. I stick exclusively to that store, and within it, I focus on items that align with her very specific aesthetic (minimalist, neutral colors, natural materials). The success rate has jumped dramatically.
For the minimalist, I’ve learned to embrace the impermanent. My brother doesn’t want more stuff cluttering his meticulously organized apartment, so instead, I focus on experiences we can share or consumables he’d enjoy but wouldn’t buy himself. Last year, I got us tickets to a specialized coffee tasting event. The gift wasn’t just the event but the shared experience and the photos I had printed afterward in a simple accordion-style mini album that could be easily displayed or stored away.
The trickiest category, though, is when the relationship itself is strained. My aunt Susan and I are on opposite ends of the political spectrum, and family gatherings can get tense. For years, I avoided meaningful gifts with her, sticking to impersonal gift cards. But that approach just reinforced the distance between us.
The breakthrough came when I stopped focusing on our differences and instead remembered what connected us. Despite our disagreements, we share a love of gardening. Last Christmas, I gave her a collection of heirloom seeds from my garden with hand-written notes about each variety and why I thought she’d enjoy them. She called me – actually called, not texted – to talk about planting strategies. It was our first non-holiday conversation in years.
The key to gifting for difficult people isn’t finding something they won’t hate – it’s looking for the intersection of meaning and usefulness that acknowledges who they are. Here’s my actual strategy:
Listen for mentions of problems needing solutions. My father once mentioned in passing that reading in bed gave him a stiff neck. Three months later on his birthday, I gave him a specialized reading pillow. He looked at me like I was psychic. I wasn’t – I just paid attention when he complained.
Pay attention to what they consistently choose for themselves. My sister-in-law always buys black and white photography books but never color ones. I found an obscure black and white collection by a photographer she hadn’t discovered yet. The delight on her face when she opened it was worth the three weeks I spent hunting it down.
Consider their routines, not just their interests. My difficult-to-buy-for boss mentioned she starts every morning with tea at her desk while checking email. I gave her a beautiful handmade mug with a lid that kept tea hot for hours (solving her constant problem of forgotten, cold tea). She uses it every single day three years later.
Sometimes, the most meaningful approach is acknowledgment without expectation. For truly complicated relationships, I’ve found that gifts focused on shared memories or family connections can transcend current tensions. A photo restored and framed. A recipe book with family traditions. These gifts say “I see our connection” without demanding reciprocity.
I’ll never forget the year I gave my cousin Mark a bound collection of scanned letters his grandfather (my great-uncle) had written during WWII. Mark and I had grown apart after a family disagreement, but I knew how much he valued family history. The letters had been sitting in my grandmother’s attic for decades. When he opened the album, the wall between us didn’t exactly come crashing down, but a window definitely appeared.
Gift-giving for difficult people isn’t actually about finding the perfect present. It’s about using the opportunity to notice someone more carefully than you might otherwise. It’s a chance to temporarily set aside the challenges in the relationship and focus solely on the person.
I’ve also learned that sometimes the most meaningful gift is respecting boundaries. My neighbor Gladys is intensely private and clearly uncomfortable receiving gifts. Rather than force the issue, I now mark occasions with a handwritten card and homemade cookies left on her doorstep – a gesture that acknowledges the day without creating the obligation of an elaborate gift.
The toughest gift scenarios have taught me patience and perspective. Not every gift will be a home run, and that’s okay. I once spent weeks tracking down a first-edition book for a difficult uncle, only to discover at Christmas that he’d recently bought the exact same edition for himself. Initially disappointed, I’ve come to see these gift “failures” as part of the learning process. (He did eventually trade his copy with mine because mine was in slightly better condition – a tiny victory I’m still unreasonably proud of.)
Sometimes, the most challenging people in our lives are difficult gift recipients precisely because the relationship itself needs attention that can’t be fixed with a present. In those cases, perhaps the gift is making a genuine effort to connect beyond the obligatory occasion.
I’ve come to believe that figuring out how to give meaningfully to the difficult people in our lives is a worthy challenge – not just because it solves the immediate problem of what to wrap and put under the tree, but because it pushes us to see past our assumptions and really notice the person behind the “difficult” label.
My father-in-law Richard and I now have an inside joke about that pike painting. Every birthday and Christmas, he asks if I’ve heard any news about “the one that got away.” It’s become our thing – a small connection point that makes family gatherings warmer and gives us something that belongs just to us in the relationship.
And really, isn’t that what we’re hoping for when we give gifts to the complicated people in our lives? Not just to check a box on a holiday obligation list, but to find our way toward a moment of genuine connection – even if it’s brief, even if it’s imperfect.
So the next time you’re staring down your gift list and feeling that familiar dread when you reach a certain name, try shifting your perspective. The difficult gift recipient isn’t an obstacle to overcome but an invitation to pay better attention. Sometimes, what you discover in the process matters more than whatever ends up wrapped with a bow.