How to Choose a Thoughtful Holiday Gift (Even When You're Not Sure What They'd Like)

Have you ever come to a name on your holiday shopping list, and have no idea what to get that peson? Maybe it's a new coworker, a partner's relative, or a friend whose taste has always been a mystery to you. The season is here, the clock is ticking, and the time for "I'll figure it out later" has long passed.

Fear not. Choosing a thoughtful holiday gift for someone you don't know well is easier when you stop guessing and work through a simple framework. The best gift-givers ask themselves the right questions before they buy anything, and those questions come down the recipient, your relationship, and the occasion.

Below, we'll explain how the answers to these questions can become a gift that lands.

Sam Maglio, a marketing and psychology professor at the University of Toronto, says that, given the lack of expectation surrounding it, everyday gift-giving can be a struggle.

"When people aren't sure about whether or not to gift, they too easily default to doing nothing," he says. "We do nothing because we overestimate how annoying or awkward it will be and underestimate how much people appreciate any gesture."

Maglio says we should view everyday gift-giving as a chance to strengthen our relationships with others rather than as a chore.

"Reappraise moments of year-round gift-giving not as an obligation but as an opportunity for connection," Maglio advises.

Here are six ways to unlock your full gift-giving potential.

Start with the recipient: What do they actually enjoy?

Being familiar with a person's hobbies and interests is the foundation of a good gift.

Sam Maglio, a marketing and psychology professor at the University of Toronto Scarborough who has researched gifting extensively, says that if you want to be an extraordinary gift-giver, you have to imagine yourself as the recipient.

"Think about what it would be like to own this gift, not just what it would be like to open this gift in the moment. What would it be like to possess this gift for a good long while?" he says. "Often, givers get it wrong because they're thinking only about the moment the recipient opens the gift. And you can't blame them; that's the part they're going to be around for. But once the surprise wears off, recipients start asking themselves, 'Am I really going to use this?'"

If you can't figure out a new friend's hobbies or a coworker's interests, perhaps you just need to get more in tune with them. From casually checking in with friends to steering a conversation toward what they've been wanting or doing lately, there are many ways to do so.

Evan Polman, an associate professor of marketing at the Wisconsin School of Business, suggests "making notes of what others say they like. Then, when it's time to get them a gift, you will already have a list of items you can surprise them with."

Listen because you care, and then show that interest by giving a thoughtful gift that proves you were paying attention.

Consider your relationship: How personal should the gift be?

A gift that's just right for your sister might feel like too much for a coworker, no matter how similar their interests might be. The closeness of your relationship is your guide to how personal to go.

Here's a quick reference for how personal to go, with one safe gift category for each relationship.

Match the occasion: What does the event call for?

Holidays have their own rhythm, and the occasion itself can guide your choice. A gift meant for a festive dinner reads differently than one meant to be quietly savored on a snowy morning at home or an office Secret Santa gift meant to be opened at the workplace. And if you'll be exchanging gifts at a big family bash, you might want to give your partner one present then and save a more intimate one to share in private.

Lead with sentiment: Why meaning beats the price tag

A gift's meaning is rarely tied to what it cost. Its real value comes from how much thought went into it and how well it fits the recipient.

"When givers take a moment to give a gift to someone else, they're acknowledging, to the recipient as well as to themselves, how much the person means to them," Maglio says. "This adds up to a real synergy of gratitude: The giver expresses appreciation for the recipient in the form of a gift, and the gift makes the recipient aware of this appreciation."

That's the quiet power of a thoughtful gift. It's a way to strengthen a relationship, to say "I see you" and "I'm glad you're in my life," all wrapped in a bow. To read more on why that connection matters, see The Psychology of Giving and the Importance of Mindful Gifts.

When your truly at a loss on what to get them

Sometimes you've worked through every question and still come up blank. Their taste is a genuine mystery, and that's okay. There are a number of reliable gifts that suit almost anyone.

A curated gift box of treats lets someone explore a range of items. A food and wine pairing turns into a shared moment at the table. A subscription sends a little surprise every few weeks, which means the thoughtfulness keeps arriving long after the holidays end.

When people aren't sure what to give or whether to give a gift at all, "they too easily default to doing nothing," Maglio notes. "We do nothing because we overestimate how annoying or awkward it will be and underestimate how much people appreciate any gesture." A well-chosen, universally loved gift removes that worry.

Here are a few reliable choices when tastes are a mystery.

Classic Everyday Sharing Gift Basket

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Founders' Favorites Gift Box

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Wine Pairing Collection - Two Bottles

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Boarderie™ Ciccetti Cheese & Charcuterie Board

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Practice makes you a better holiday gift-giver

The more you practice thoughtful gifting throughout the year, the easier the holidays become. Giving a "just because" gift, a get-well-soon surprise, or a congratulations on a promotion all sharpen the same instincts you'll use come December. Practicing this kind of unexpected generosity encourages creativity, making you look past the usual holiday go-tos and consider a wider range of options.

Maglio suggests viewing gifting "not as an obligation but as an opportunity for connection." So when the holidays roll around, everything you've learned from a year of small, thoughtful gestures will make your gifts more meaningful.