How to Figure Out Which Gifts They Actually Want, a Conversation Guide

November 23, 2016

Day 5 of 30 Days of Thoughtful Giving: How to be a more thoughtful eavesdropper.

It's the day before Thanksgiving and all through the house, every creature is stirring—and baking, and roasting, and doing fridge-checks for the final (okay, second-to-last) grocery run.

Now, meaning all weekend long, is your chance to eavesdrop on all your loved ones to figure out what might be the perfect gift for each of them. Find a notepad or clear some brain space: We've rounded up some helpful leading questions and things to listen for while you're with your loved ones all weekend, for maximum "I know the perfect gift!" moments.

Photo by James Ransom

leading questions

Drop these like they're hot, and then listen up.

Do you have any fun trips coming up?

If yes, consider a gift that would be useful for their trip or for travel in general: a nicer toiletries pouch, a lightweight bag that folds up to a pouch for stowing souvenirs they accumulate, or an insulated water bottle. If they don't have any trips coming up, see here.

How's work going?

Read the response carefully. If it's buoyant, play into their high: a new notebook for your budding journalist niece, or a wool beanie for the wildlife photographer uncle. If they say "same as always" and seem bored with the topic, think of something to perk up their desk life: a little brass bud vase or a coffee mug to leave at the office. And if they seem stressed, a gift certificate for a massage or a fancy loofah and some DIY bath soak wouldn't be amiss.

Tell me what's your apartment like.

Obviously, save this for the folks you haven't (YET) visited—ideally they'll need to show you some pictures, as well. Look closely: If you spot fresh flowers, a vase or a flower subscription would be an amazing idea. And listen, too: Have they "been meaning to get some cute wall hooks" to go by the door? (We've got 'em.)

How are you spending your time outside of work these days?

In this case, you're fishing for hobbies: Give reams of new, beautiful yarn to the sister who has taken up knitting. Or a gift certificate to an indie movie theater for a film junkie. Proper linen napkins for the cousin who just moved in with her boyfriend.

I need some new recipe ideas! Have you found any great recipes recently?

The illusion here is that you're just fishing for recipe ideas for yourself, you sly fox you, but what you're really doing (right?) is listening: Is your dad on an ancient grain kick? (It's a thing.) Get him a wee stovetop rice cooker, which makes perfect rice, quinoa, farro—okay, any grain. Your mom is going through a salad phase? Get her a big beautiful bowl to eat them out of.

Or maybe they're all about baked good, all the time: This is a spectacular cookbook, and gift, but you could also just make them an almond coffee cake.

Or get a mini-griddle for the breakfast-obsessed, or nifty ice cube trays for anyone who recommends you try this new drink they discovered called a Negroni.

things to listen for

A compliment of something you own.

  • With you've got helping hands in the kitchen, listen up: "Oh, I love these kitchen shears! Mine aren't sharp anymore" or, "I'm kind of obsessed with this nonstick skillet—it does everything!" are what I like to call "lay-ups." And if whatever they love is on the pricier side, rope another family member in to split it with you: Look, you've made another person happy, too!
  • The same goes for overnight guests, perhaps even more so. Are they obsessed with the hair dryer you didn't even realize was in the guest room? They need a new one. Can they not stop complimenting how comfy the bed is? Get them new linen sheets (or even linen pillowcases). Or, they're enamored with how your fancy coffee tastes? Buy them a subscription for better beans, or a pour-over setup if they're still working with a drip coffee maker at home.


  • Turn the unfortunate likelihood that one of your loved ones will voice a complaint into a clue: "I'm so bored with [insert small hometown he/she still lives in]" is the perfect excuse to do some investigating and get them a gift certificate to the newest restaurant in town. Groans about housework—"I feel like I'm constantly doing laundry" or "Ugh, I just wish we had a dishwasher"—call for wooly dryer balls, or reusable pot scrubbers, or a drying rack that's actually good-looking.

Timely announcements of things "they're into."

This might sound too good to be true—loved ones who actually drop hints without you prompting them? But what you're actually listening for are those boastful, sometimes backhanded remarks that we so often tend to spew when we're trying to impress or one-up. After a long weekend of hanging out together, you might hear...

  • "I'm really into poached eggs right now," from your aunt, as you slide plain old scrambleds onto her plate. Get her an egg coddler. (Actually, just get everyone an egg coddler—they're awesome.)
  • "I've gotten really into gardening," your uncle might say as you sit on the back porch regarding your half-dead back yard. Get him new shears.
  • When you put a bottle of hot honey out with biscuits, someone might claim "we totally discovered hot honey before it became such a thing!" In which case, give them Spicy Maple Syrup. (Take that.)

It's the end of a long weekend of occasionally awkward conversation and you know that—underneath even the snidest remarks—your loved ones (most likely) mean well. Nudge them into telling you what they want and need, listen up, and the glee you'll incite, when they realize you were thinking of them all along, will put everyone in the holiday spirit.

How do you get your loved ones dropping gift hints? Tell us in the comments.

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Amanda Sims

Written by: Amanda Sims

Professional trespasser.

1 Comment

Sam December 9, 2016
I love how all of these examples seem like moments that have actually happened at your family's gatherings, Amanda. Brilliant writing (or maybe just great retelling of memories?).