It’s a uniquely uncomfortable feeling: the gift exchange moment when you realize you’ve been outdone, big time. I remember one anniversary, I thought I’d found the perfect gift for my partner with a bulk order of astronaut ice cream. It seemed ideal – he loves the stuff, it’s quirky, and I got a mountain of it.
Then he presented his gift: a commissioned miniature watercolor painting. Months of work by a specialized artist, depicting my favorite Google search: “owls kissing.” (Yes, I know, saccharine, but try to find anything sweeter.) The astronaut ice cream, while fun, paled in comparison. It would have been a great, random Tuesday gift, but the occasion highlighted the hilarious gap between our presents. While I believe intention is key in gift-giving, sometimes a do-over would be welcome, especially when aiming for that perfect gift.
This year, I’m determined to elevate my gift-giving game and find truly exceptional presents. Maybe aiming to be the ultimate gift-giver is a bit much, but learning to give better, more perfect gifts? That’s a worthy goal. So, I consulted gift-giving and etiquette experts to uncover their strategies for brainstorming, creative thinking, and finding that elusive perfect gift.
“I’ve always thought that literally anything, any object, even trash, can be the perfect gift,” says Helen Rosner, a staff writer at The New Yorker known for her wonderfully eccentric and genuinely helpful annual food-themed gift guide. “It could be a simple Tootsie Pop or a $10,000 diamond cocktail shaker. The secret is matching the right thing to the right person.”
Wild Little Owls Kissing: A heartwarming image of two young owls sharing a tender moment, perfect for expressing affection and tenderness in a gift.
Meaningful Gifts Don’t Have to Be Extravagant
Whether you’re considering a $10,000 cocktail shaker or something more modest, the quest for the perfect gift can quickly become overwhelming. Before you even start browsing, remember this: a truly successful gift doesn’t need to be earth-shattering to be considered perfect.
“We often put pressure on ourselves to find that one gift that only we could give, the gift that proves how well we know them. That’s almost impossible,” explains Erica Cerulo, co-host of the A Thing or Two podcast and newsletter, filled with thoughtful recommendations, with her business partner, Claire Mazur. (They previously co-founded the retail site Of A Kind.) A great gift, Cerulo emphasizes, doesn’t have to be life-altering. It just needs to be enjoyable, pleasant, or comforting – a perfectly nice gift in its own right.
Similarly, a meaningful and perfect gift isn’t defined by its price tag. Rosner shared a story about a family book swap last winter. Each person chose a book from their own shelf they thought someone else would enjoy. “Part of the gift was explaining why: ‘I read this, I loved it, and I think you’d love it,’” Rosner recalls. “It cost nothing, sparked great conversations, and felt incredibly personal and meaningful.” This demonstrates how a truly perfect gift can be priceless.
The Three Pillars of Perfect Gift-Giving
To channel creativity, Cerulo offers a helpful three-point framework for approaching gift-giving. Ask yourself: “Can I introduce them to something new they might not discover otherwise? Can I give them an upgraded version of something they’d buy for themselves? Or, can I make them feel truly seen and understood?” If you can answer yes to one of these, you’re likely on the path to finding a perfect gift.
Mazur shared a story illustrating this. After staying with generous hosts who cooked every meal, “We realized we kept running out for seltzer water all weekend. So, we sent them a really nice seltzer maker afterward,” Mazur says. “When we visited again, it was in constant use, and even their kids had learned how to use it.” She describes this as a particularly rewarding gift-giving experience that ticked several of Cerulo’s boxes. It was something their hosts probably wouldn’t splurge on for themselves (a touch of luxury in endless seltzer) and showed Mazur was paying attention to their habits. This thoughtful observation led to a perfectly practical and appreciated gift.
Making someone feel seen is at the heart of why we give gifts. “Gift-giving is a way to express love by reflecting back who they are and showing them how we see them,” Rosner explains. You could opt for a $70 crystal whiskey glass, or you could hunt down those vintage Pizza Hut Flintstones Kids glasses from the 1980s they adored as a child. The latter, though less expensive, speaks volumes about knowing the recipient and finding a truly perfectly nostalgic gift.
So, how do you tap into this level of knowing someone? It starts with being prepared…
The Secret Weapon: A Running Gift Idea List
Most exceptional gift-givers do their homework year-round, not just in the weeks before a birthday or holiday. Many keep ongoing lists of potential gifts for loved ones, updated whenever someone mentions something they desire or when they stumble upon a great gift idea. Your system can be whatever works best: Cerulo uses a single note on her phone, Mazur keeps separate notes for each person, and Rosner uses contact notes to track preferences, birthdays, and gift ideas. This proactive approach is crucial for consistently finding perfect gifts.
If a friend’s interests lean toward vintage or handmade items, consider setting up alerts on sites like Etsy and eBay. Early in their relationship, Cerulo’s husband spent years searching eBay for a vintage Vogue cover from the 1940s designed by Salvador Dalí. It was a long game, but incredibly meaningful when Cerulo received it. Working in magazines at the time and obsessed with that particular cover since seeing a Dalí exhibit in college, “It just felt like, ‘Right. You get it,’” Cerulo remembers. This dedication and personalization resulted in a truly perfect and unforgettable gift.
Having a system for collecting gift ideas also helps you avoid directly asking loved ones what they want – something Crystal L. Bailey, director of the Etiquette Institute of Washington, advises against. “It puts the burden on them to figure out their own gifts. Instead, we should really try to notice what someone appreciates and enjoys,” she says. Observing and noting these details throughout the year is key to discovering truly perfect gifts that resonate.
Craft a Mini-Bio for Close Friends and Family
Finding the perfect gift for those closest to us can paradoxically be the most challenging. How do you capture your sister’s unique essence in a single present? First, abandon grand gestures. Second, gain perspective using a technique Mazur and Cerulo developed for creating gift guides: write a short, three-sentence bio of the person, focusing on their passions, obsessions, and interests. “I might write, ‘My dad is a sports fanatic, thinks most kitchen gadgets are pretentious, and has been a lawyer his entire career,’” Mazur explains. “This creates more space for imaginative gift ideas.” This exercise helps to move beyond generic gift categories and pinpoint a truly perfectly tailored gift.
If you’re familiar with gift guides, this exercise also helps you avoid pigeonholing loved ones into consumer profiles. (Gift guides can sometimes reduce men’s interests to whiskey stones and beard oil.) “It’s better to give something that says, ‘This is a gift for you’ – for you as an individual, not as a demographic,” Rosner says. “Like, ‘I know you love Nutter Butters, so here are 17 packages of Nutter Butters.’” This level of specific attention is what transforms a good gift into a perfect gift.
Thoughtful Gifts for Acquaintances
For people you don’t know well, Bailey recommends personalized yet not overly personal gifts. For a coworker, a signed card and a gift card related to their interests is a good choice. Perfumes, scented items, and clothing can be too intimate. The goal is to find a perfectly appropriate gift that acknowledges the relationship without overstepping.
This reflects a fundamental truth about gifts for your boss or your partner’s new sibling: deep intimacy isn’t necessary, and that’s perfectly okay. “When it’s someone you don’t know very well, you don’t need to go through this elaborate process of reflecting their inner self back to them because you don’t have that insight yet,” says Rosner. “This is a different kind of gift communication where it’s simply, ‘I want to give you something that brings you a little joy.’” The aim is a perfectly pleasant gift that shows consideration.
In these situations, knowing just one personal detail can be enough. “It could be something deep like, ‘She’s really into pre-Prohibition cocktails,’ or something simple like, ‘I know her favorite color is lilac,’” Rosner suggests. Avoid “gift mansplaining” – giving a beginner item related to their interest, like Joy of Cooking to a chef – or something so obscure it seems like you’re trying to impress. For the cocktail enthusiast, perhaps the best ice cube mold recommended by cocktail experts – a small gesture showing you put thought into finding a perfectly suitable and quality gift.
Reliable Gift Categories When You’re Stuck
Several gift categories consistently emerged in my expert interviews as reliable choices. Consider this your cheat sheet for finding a dependably perfect gift.
Books
Like Rosner, Cerulo and Mazur see books as fostering connection, regardless of familiarity with the recipient. Gift a book you’ve loved or one aligning with their interests (cookbook, mystery, birdwatching guide). “It builds longer-term relationships in a way other gifts don’t,” Cerulo says. A thoughtfully chosen book can be a perfectly enriching gift.
Food, Drinks, and Consumables
Bailey favors gifts that avoid adding clutter. Food is ideal. It can be personal and nostalgic (Skyline Chili shipped to a Cincinnati native via Goldbelly), luxurious yet affordable (specialty salt or olive oil), or homemade (Cerulo’s husband’s annual eggnog for friends). Consumables are often perfectly practical and delightful gifts.
The Biggest Version Possible
A shortcut to a great gift: if they love something, give them a lot of it. Absurd volume is funny, insightful, indulgent, and a bit teasing. Think a giant box of pink Starbursts, or Mazur’s “several-gallon jug” of Red Boat Fish Sauce from Cerulo.
“One pair of socks is sad. Five pairs is dutiful. Ten starts to get interesting,” Rosner says. “But 100 is hilarious. That’s what makes it a great gift. You have to cross that line.” Going big can turn a standard item into a perfectly memorable and fun gift.
By focusing on thoughtfulness, observation, and understanding the recipient, finding the perfect gift becomes less daunting and more rewarding. Remember, the most perfect gifts are those given with intention and care, creating connection and joy for both giver and receiver.
