It’s a special kind of agony to realize, while exchanging gifts with someone, that they got you something way, way better than what you got them. A few years ago, I bought for my partner what I thought was a perfect anniversary gift: a bulk order of astronaut ice cream. In many ways, I nailed it. He loves freeze-dried ice cream, which you rarely see in the wild outside of science museums, and I had gotten a comical number of packages.

The problem is that his gift for me was an all-timer, a miniature painting that he had commissioned from an artist who specializes in painstakingly detailed watercolors. He had worked on it for months, and the image illustrated my favorite Google search: “owls kissing.” (Saccharine, I know, but I dare you to find me anything cuter.) Astronaut ice cream would have been an amazing present if given on a random Tuesday, but the occasion and the wild discrepancy between our gifts was hilarious and vaguely horrifying. I do believe that intention matters more than execution with gifts — that it doesn’t really matter what you give someone, as long as you put thought and love into it — but sometimes it would be nice to get a do-over.

This holiday season, I am out for blood, and by blood, I mean really good presents. Is transforming myself into the best gift-giver of all time too much to ask? Probably. In the interest of merely learning how to give better presents, I turned to several experts in the arts of gift-giving and etiquette, who shared their tactics and frameworks for gathering ideas and getting in a creative mindset.

“I’ve always believed that literally anything on earth, any object, any piece of trash, anything you find in a store, can be a perfect gift,” says Helen Rosner, a New Yorker staff writer who publishes an annual food-themed gift guide that is somehow both deranged and genuinely useful. “It can be a Tootsie Pop or a $10,000 diamond-encrusted cocktail shaker. What’s important is matching the right thing to the right person.”

Whether or not you’re in a position to buy a $10,000 cocktail shaker, it’s remarkably easy to start spiraling about finding the perfect gift for someone. Before you open a single browser tab, take a minute to remember that a gift doesn’t have to cause absolute emotional devastation (in a good way) in order to be successful.

“We often give ourselves this challenge of being like, ‘What is the gift that only I could give them? What is the gift that proves I know them so well?’ And that’s kind of impossible,” says Erica Cerulo, who runs the recommendation-filled A Thing or Two podcast and newsletter with her business partner, Claire Mazur. (Cerulo and Mazur previously co-founded the retail destination Of A Kind, which shut down in 2019.) A great gift doesn’t have to change someone’s life, Cerulo says: It can just be something that’s fun and nice and comforting.

Similarly, you don’t have to spend a certain amount of money for a gift to feel meaningful. Rosner did a book swap with family last winter, wherein each person had to choose a title from their own shelf that they thought another person in the group would enjoy. “Part of the gift was explaining: ‘I have read this, I loved it, and I think you would love it,’” Rosner says. “It involved spending zero dollars, it created amazing conversations, and it felt really personal and deep.”

Because creativity thrives with constraints, Cerulo offered the following three-point framework for thinking about gift-giving: “Can I introduce someone to something they might not otherwise know about? Can I get them a nicer version of something than they would buy for themselves? Or can I make them feel seen?” If you can check one of those three boxes, you’ve probably got a good present on your hands.

Last summer, Cerulo and Mazur went to stay with some friends who were very generous hosts, cooking every meal. “All weekend we were running out for seltzer water, so afterward I sent them a really nice seltzer maker,” Mazur says. “We came back, and it was in use all weekend, and the kids had learned how to use it.” She describes this as a particularly satisfying gift-giving experience that ticked several of the boxes Cerulo laid out. It was something their hosts probably weren’t going to buy for themselves (and was luxurious in a way that only infinite seltzer can be), and it demonstrated that she was paying attention to their habits.

Making someone feel seen gets to the reason why we give people gifts in the first place. “The way that we express love to people through gift-giving is by reflecting who they are back to them, and also by showing them who we see them as,” says Rosner. You could get someone a $70 cut-crystal glass for their whiskey, for instance, but you could also track down the Pizza Hut Flintstones Kids glasses from the 1980s that they loved as a child.

So how do you make someone feel known? Unlock your phone and ...

Almost universally, great gift-givers are doing legwork throughout the year, not just in the weeks leading up to a birthday or major 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 turn up a particularly great present idea. You can do this in any way that suits you: Cerulo has a single note in her phone dedicated to gift ideas, Mazur keeps individual notes for individual people, and Rosner uses friends’ contacts as a place to log food preferences, birthdays, and present ideas.

If a friend mentions an interest that lends itself well toward vintage or handmade products, you may also consider setting up alerts on that subject on sites like Etsy and eBay. In the earlier years of their relationship, Cerulo’s husband used eBay to hunt down a vintage Vogue cover from the 1940s that was designed by Salvador Dalí. It was a long con that took him several years, but it was incredibly meaningful to Cerulo when she received it: She worked in magazines at the time and was obsessed with that particular cover, having seen an exhibit of Dalí’s art while studying abroad in college. “It just really felt like, ‘Right. You get it,’” Cerulo recalls.

Incidentally, devising systems for gathering gift ideas can help you steer clear of asking your loved ones what they want — something that Crystal L. Bailey, director of the Etiquette Institute of Washington, suggests avoiding. “It puts the onus on them to kind of figure out their own gifts, right? So if we can, in our relationships, really try to take notice of what someone appreciates and what they enjoy,” she says.

Our closest confidantes are sometimes the most challenging people on our list. How are you supposed to distill your sister’s marvelous and unique essence into a single package? First, step away from the grandiose thinking. Second, get some perspective with a tactic that Mazur and Cerulo figured out while creating gift guides: Write a three-sentence description of the person you have in mind, paying close attention to their enthusiasms, obsessions, and interests. “I might say, ‘My dad is obsessed with sports, he thinks most kitchen gadgets are pretentious, and he’s been a lawyer his whole life,’” says Mazur. “Then there’s a little bit more room to get imaginative.”

If you’ve spent a lot of time looking at gift guides, this exercise can also help you break out of thinking about your loved ones in terms of consumer profiles. (I like gift guides, but they do have a tendency to, say, boil men’s interests down to whiskey stones and beard oil.) “It’s better to give something that’s like, ‘This is a gift for you’ — like you as a person, not you as some demographic category,” says Rosner. “I know you love Nutter Butters, so here are 17 packages of Nutter Butters.”

From an etiquette standpoint, Bailey advises personalizing gifts to people you don’t know very well, without getting too personal. For a co-worker, a signed greeting card and a gift card aligned with their interests can be a good option. Perfumes, scented items, and clothing, on the other hand, can be a little too intimate.

This philosophy gets at a fundamental truth about buying a gift for your boss or your brother’s new honey: You’re not close friends, and that’s actually fine. “When it’s someone you don’t know super well, you don’t have to go through this crazy dance of trying to reflect themselves back at them and also the way you see them, because you don’t have that yet,” says Rosner. “This is a totally different type 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 one personal fact about the recipient. “It could be as deep as, ‘She’s really into pre-Prohibition cocktails,’ or it could be as shallow as, ‘I know her favorite color’s lilac,’” Rosner says. Avoid giving someone “the gift equivalent of mansplaining” — i.e. an entry-level item pertaining to their interest, like the Joy of Cooking for an amateur chef — or buying them something so esoteric that it looks like you’re trying to one-up them. For the cocktail aficionado, you might just find them the best ice cube mold, according to cocktail experts — a little gesture to show that you care to buy them something of quality.

Several kinds of presents kept coming up in my interviews, so I’ve compiled them here. Consider this your cheat sheet to buying a reliably good present.

Books

Like Rosner, Cerulo and Mazur see books as an opportunity to bond with the recipient, whether or not you already know them well. You can give someone a book that you’ve read and loved, or you can buy them one that’s in line with their interests (a cookbook, a mystery novel, a birdwatching tome). “It creates longer-term relationship building that other things don’t,” says Cerulo.

Food, beverages, 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 ex-pat via Goldbelly), decadent but not ridiculously expensive (special salt or olive oil), or lovingly made at home (Cerulo’s husband prepares eggnog every year and bottles it for friends).

The biggest version of the thing possible

Here’s a shortcut to a great gift: If you know that someone loves a particular item, just get them a ton of it. Absurd volume is funny, knowing, luxurious, and a little bit teasing. It could be a huge box of pink Starbursts, or, as Cerulo once bought for Mazur, a “several-gallon jug” of Red Boat Fish Sauce.

“One pair of socks is tragic. Five pairs of socks feels dutiful. Ten starts to be a little interesting,” Rosner says. “But 100 is ludicrous. And that’s what makes it a great gift. You have to cross that line.”