What Gifting Experts Get People Who Are Hard To Shop For

We all have someone on our holiday gift list who gives us a twinge of dread. Maybe they express their opinions about what they’ve gotten a bit too readily (or harshly), or it seems impossible to give them something they don’t already have. In those cases, shopping becomes a challenge instead of something enjoyable.

But according to experts, it doesn’t have to be this way. Jessica Furr, founder of the curated gift guide Muse, has a technique she uses in these situations: Notice, Expand, Transform, Delight. “The hard-to-shop-for person is usually someone with strong taste or a specific habit,” she explains “The best gifts come from something you’ve seen them do repeatedly.” 

Jerina Vincent, founder of JNJ Gifts & More, works with corporate clients and individuals to create thoughtful gifts for clients, employees, executives, and people who are simply hard to shop for. She recommends considering the person rather than the product first. “I usually don’t start by asking, ‘What can I buy them?’ I think about the person first,”” she says, then asks, “What do they enjoy? What would make them feel seen or appreciated?”

With that in mind, here are their tips, which are sure to help you find the perfect gift for that picky giftee on your holiday shopping list. (Our experts told us the types of gifts they’d give, and we added our favorite picks, along with additional products based on their advice. They did not endorse specific products.)

An Experience or Skill-Building Gift

“Gifts that show you put time into them are the ones people treasure,” Furr says. That’s why she recommends skill-building or experience gifts, chosen based on your loved one’s personality or specific interests. 

Companies like Xperience Days allow you to choose gifts to experience in person. You can enjoy an activity together, whether it’s a beer-tasting tour, a cooking class, or a lunch or dinner cruise. Giftory and Wonder Box are other options that let you purchase giftable experiences in select cities nationwide. These options come in a nice envelope, so you have a physical item to give. Just research your giftee’s location in advance to ensure they have options in or near their area.

An Experience in a Box

If you prefer to buy a physical object, Furr recommends choosing a kit. For example, a cheese lover who also enjoys cooking or crafting may love something like the Big Cheese Ultimate Cheese Making Kit. An artist or creative type may appreciate this KURUMi Custom Paint-by-Numbers Kit featuring one of your favorite photos together. It’s even better if you find a kit you can do together, so that “the time you spend is the gift,” Furr says.

Vincent recommends curating selections for different themes: “That is what makes the gift memorable,” she says. “You are not just giving products. You are giving the recipient a moment they can enjoy.” One idea is a movie-night box — which she says could include a “personalized popcorn bowl, premium popcorn, a blanket, and a streaming gift card” — or a custom gift box inspired by cold weather. “I might pair hot cocoa, marshmallows, a mini portable firepit, and a soft blanket,” she says. “Each item makes sense on its own, but together they create a complete cozy evening experience.”

If you prefer a premade gift set, consider selections such as the Urban Accents Movie Night Popcorn Gift Set or the Stonewall Kitchen New England Breakfast 6-Piece Gift Set.

A Gift They Can Use

If you don’t know a person well enough to expand on an existing hobby or personal interest, Furr says you should choose something they’ll use up, not a thing they’ll accumulate. Selections like a “candle or good coffee need no read on their taste,” she says. 

You can opt for a high-end candle from Quince, which has holiday scents like Pumpkin Cardamom and Spiced Noël, or go for something outside the box, like these Unscented Totem Pillar Candles from Creative Co-Op. Coffee from premium brands, such as the Bean Organic Coffee Co. or Java Planet, make for fanciful gifts for the javaphile. You can even include a fancy to-go mug, like this spill-proof option by Contigo, if they need an upgrade for sipping outside the home.

Food-Related Gifts

Vincent also likes food gifts, “especially when they create an experience and when the products are high quality,” she says. “Breakfast gifts have been very successful for us because they are easy to enjoy and often become something the whole family can share. We may pair artisan pancake mix with coffee, maple syrup, pecans, chocolate, or a diner-style mug.”

It’s tempting to load up a gift box you’re curating with a ton of products, but Vincent advises against this. “I would rather use four or five really good items that work together and create one clear experience,” she says. “That is usually what people remember: how we made them feel when they received it!”

You can also opt for a few premade curated options, such as assorted nuts, meat-and-cheese samplers, hot chocolate varieties, or a hot sauce gift set.

Something Based on a Specific Hobby or Routine

Your giftee’s hobby, or even a specific routine or ritual, can help guide gift ideas. “Go one level deeper into a hobby: not the hobby itself, but the nicer accessory they’d never buy themselves,” Furr says. 

Vincent concurs, noting that picking a gift “around a recipient’s hobby can feel more personal than simply adding their initials to an item.” For example, if they picked up pickleball this year, you might consider a brand-new paddle or upgraded footwear. Someone who loves cooking might appreciate a quality recipe notebook to write down family recipes that live only in their memory. And the new bird-watcher in your life may get excited about a smart bird feeder that helps them easily identify the feathered friends visiting their home.

Personalized Gifts

Personalized gifts can also resonate. Vincent says she prefers useful and subtle personalization, “such as a name on a serving piece, popcorn bowl, travel accessories, or keepsake box.” And don’t forget a note, which she says is “one of the most important parts of the gift.”

According to Furr, “gifts that show you put time into them are the ones people treasure.” You may get a custom vinyl, featuring a list of favorite songs or ones inspired by a special time you’ve spent together; create a custom brainteaser; or add a collection of photos to a viewfinder to give them a nostalgic look back at the good ol’ days. 

That one difficult person may be a challenge, but with the right perspective and insight as you shop, you can find a gift that resonates with them and leaves a lasting (and hopefully positive!) impression.

_{Featured Image Credit: Products courtesy of vendors}