It’s a special kind of agony to realize, while exchanging gifts with someone, that they’ve gotten you something much, much better than what you gave them. A few years ago, I bought my partner what I thought was the perfect anniversary gift: a large order of astronaut ice cream. In many ways, I nailed it. He loves freeze-dried ice cream, which is rarely seen in the wild outside science museums, and I had received a comical number of packets.
The problem is, his gift to me was a jack of all trades, a miniature painting he’d commissioned from an artist who specializes in painstakingly detailed watercolors. She had been working on it for months and the image illustrated my favorite Google search: “kissing owls.” (Saccharine, I know, but I dare you to find me anything cuter.) The astronaut ice cream would have made a fantastic gift if given on a random Tuesday, but the occasion and the wild mismatch between our gifts was hilarious and vaguely awful. I believe that intention is more important than execution with gifts — that it really doesn’t matter what you give someone as long as you put thought and love into it — but sometimes it would be nice to do a makeover.
This holiday season, I’m out for blood, and by blood, I mean nice presents. Is turning me into the best donor of all time too much to ask? Probably. In the interest of simply learning how to give better gifts, I reached out to several experts in the arts of gift giving and etiquette, who shared their tactics and frameworks for brainstorming ideas and entering a creative mindset.
“I’ve always believed that literally anything on earth—any object, any piece of junk, anything you find in a store—can make a perfect gift,” says Helen Rosner, a New Yorker writer who publishes an annual food themed gift guide which is somehow both deranged and genuinely helpful. “It can be a Tootsie Pop or a $10,000 diamond-encrusted shaker. The important thing is to match the right thing to the right person”.
Not all gifts have to be life-changing, and a meaningful gift doesn’t have to cost a lot of money
Whether or not you’re able to buy a $10,000 cocktail shaker, it’s remarkably easy to start spiraling around finding the perfect gift for someone. Before opening a single browser tab, take a minute to remind yourself that a gift doesn’t have to cause absolute emotional devastation (in a good way) to be successful.
“Often we give ourselves this challenge by asking ourselves: ‘What is the gift that only I could give them? What is the gift that proves that I know them so well?’ And it’s nearly impossible,” says Erica Cerulo, who runs the recommendation-filled program A thing or two podcasts and newsletters with his business partner, Claire Mazur. (Cerulo and Mazur previously co-founded retail destination Of A Kind, which closed in 2019.) A great gift doesn’t have to change someone’s life, Cerulo says: It can just be something fun, cute, and comforting. .
Likewise, you don’t have to spend a certain amount of money for a gift to be meaningful. Rosner did a family book swap last winter, in which each person had to choose a title from their shelf that they thought another person in the group would like. “Part of the gift read, ‘I read this, I loved this, and I think you would love this,’” says Rosner. “He involved zero dollar spending, created amazing conversations, and felt really personal and profound.”
Try ticking one of the three gift boxes
Because creativity thrives on constraints, Cerulo offered the following three-point framework for thinking about gift giving: “Can I present someone with something they might not otherwise know about? Can I get them a better version of something than they would buy themselves? Or can I make them feel seen? If you can check one of these three boxes, you probably have a nice gift on your hands.
Last summer, Cerulo and Mazur stayed with some friends who were very generous hosts, cooking every meal. “We were running out of seltzer water all weekend, so I sent them a really nice seltzer maker afterward,” says Mazur. “We came back and it was used all weekend and the kids learned to use it.” He describes this as a particularly satisfying gifting experience that ticked many of the boxes Cerulo ticked. It was something their guests likely wouldn’t buy for themselves (and it was luxurious in a way only an endless seltzer can be), and it showed that he was paying attention to their habits.
Making someone feel seen gets to why we give people gifts in the first place. “The way we express love for people through giving is by reflecting who they are and also by showing them how we see them,” says Rosner. You could give someone a $70 cut crystal glass for their whiskey, for example, but you could also trace the Pizza Hut The Flintstones boys eyeglasses from the 80s that they loved as children.
So how do you make someone feel known? Unlock your phone and…
Keep an updated list of gift ideas
Almost universally, major donors do their footwork throughout the year, not just in the weeks leading up to a birthday or milestone holiday. Many keep lists of potential gifts for their friends and loved ones, which they update every time someone mentions an item they’d love, or when their Internet travels reveal a particularly great gift idea. You can do it any way you like: Cerulo has a single note in his phone dedicated to gift ideas, Mazur keeps individual notes for individual people, and Rosner uses friends’ contacts as a place to record food preferences, birthdays, and gift ideas.
If a friend mentions an interest that lends itself well to vintage or handmade products, you might also consider setting up alerts about that topic on sites like Etsy and eBay. In the early years of their relationship, Cerulo’s husband used eBay to hunt down a vintage 1940s Vogue cover designed by Salvador Dalí. It was a long scam that took him several years, but it was incredibly meaningful to Cerulo when he received it – he was working in magazines at the time and was obsessed with that particular cover, having seen an exhibition of Dalí’s art while studying abroad in college . “It really felt like, ‘Right. You got it,’” recalls Cerulo.
Incidentally, devising systems for collecting gift ideas can help you avoid asking loved ones what they want — something Crystal L. Bailey, director of the Etiquette Institute of Washington, suggests to avoid. “It puts the onus on them to figure out their own gifts, right? So if we can, in our relationships, we really try to take note of what someone values and what they like,” he says.
Write a mini-bio of the recipient, even if you know them well
Our closest confidants are sometimes the hardest people on our list. How are you supposed to distill your sister’s beautiful and unique essence into one package? First, step away from grandiose thinking. Second, gain perspective with a tactic Mazur and Cerulo devised when creating gift guides: Write a three-sentence description of the person you have in mind, paying close attention to their enthusiasts, obsessions, and interests. “I could say, ‘My dad is obsessed with sports, he thinks most kitchen gadgets are pretentious, and he’s been a lawyer all his life,’” says Mazur. “Then there’s a little more room to be imaginative.”
If you’ve spent a lot of time looking at gift guides, this exercise can also help you stop thinking about your loved ones in terms of consumer profiles. (I like gift guides, but they have a tendency to, shall we say, reduce men’s interests to whiskey stones and beard oil.) “It’s best to give something like, ‘This is a gift for you‘ — like you as a person, not as a demographic,” says Rosner. “I know you love Nutter Butters, so here are 17 packets of Nutter Butters.”
Don’t worry about gifts for people you don’t know well
From an etiquette perspective, Bailey recommends personalizing gifts to people you don’t know very well, without getting too personal. For a coworker, a signed greeting card and gift card that aligns with your interests may be a good option. Perfumes, scented objects and clothing, on the other hand, can be a little too intimate.
This philosophy comes down to a fundamental truth about buying a gift for your boss or your brother’s new sweetie: You’re not close friends, and that’s actually okay. “When it comes to someone you don’t know very well, you don’t have to go through this crazy dance of trying to self-reflect about them and also how you see them, because you haven’t got it yet,” says Rosner. “This is a whole different kind of gift communication where it’s just like, ‘I’d like to give you something that makes you a little bit happy.'”
In this situation, you just need to know a personal fact about the recipient. “It could be profound like ‘She really likes pre-Prohibition cocktails’ or it could be shallow like ‘I know her favorite color is lilac,’” says Rosner. Avoid giving someone the “gift equivalent of mansplaining” – i.e. an entry-level item relevant to their interest, such as the Joy of cooking for an amateur chef – or buying them something so esoteric it seems like you’re trying to outdo them. For cocktail aficionados, you might just find them the best ice cube tray, according to cocktail experts – a small gesture to show you care about buying them something quality.
If in doubt, turn to one of these categories
Different kinds of gifts kept popping up in my interviews, so I’ve rounded them up here. Consider this your cheat sheet for buying a reliable gift.
Like Rosner, Cerulo and Mazur see the books as an opportunity to bond with the recipient, whether or not you already know them well. You can give someone a book you’ve read and loved, or you can buy one that fits their interests (cookbook, mystery novel, birdwatching book). “It creates long-term relationships that other things don’t,” says Cerulo.
Food, drinks and other consumables
Etiquette-wise, Bailey is a big fan of gifts that avoid encumbering the recipient with clutter. Food is a great version of that. It can be personal and nostalgic (Skyline Chili shipped to a Cincinnati expat via Goldbelly), decadent but not ridiculously expensive (special salt or olive oil), or lovingly made at home (Cerulo’s husband makes eggnog every year and bottles it for friends).
The biggest possible version of the thing
Here’s a shortcut to a great gift: If you know someone loves a particular item, get lots of them. Absurd volume is fun, self-aware, luxurious, and a little tantalizing. It could be a huge box of pink Starbursts or, as Cerulo once bought for Mazur, a “multi-gallon jug” of Red Boat Fish Sauce.
“A pair of socks is tragic. Five pairs of socks feel like a must. Ten is starting to get a little interesting,” says Rosner. “But 100 is ridiculous. And that’s what makes it a great gift. You have to cross that line.
Elisa Brooke is a freelance journalist covering design, culture and entertainment.
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