Find the Perfect Gift Challenge

A global pandemic certainly ups the challenge of what’s already a stressful task: buying the perfect holiday gift for everyone on your list. We decided to lean into this challenge in a big way. We asked for ideas on Instagram, and to make it a true challenge, we tried to stay away from Amazon, threw in lots of ways to support small and local businesses, and tackled scenarios that are unique to 2020.

Lonely Heart

Smaller holiday gatherings are a bummer, but negotiating the holidays solo is really tough. These gifts bring companionship and cheer to loved ones who have spent a lot of time on their own this year.

Connect with a Master – Laura and Marjie both both love our subscriptions to Masterclass. It’s a learning library where people at the very top of their field give lessons on how they achieved their success. Even if you don’t expect to skateboard like Tony Hawk or write like Joyce Carol Oates, the intimate, fascinating videos will leave you feeling like you’ve had a great chat with an inspiring friend. An annual subscription gives access to over 90 classes. $180 per year (but check for deals), masterclass.com —MK, LH

Window Bird Feeder – Our feathered friends provide great company too. This stylish glass and brass feeder attaches to the exterior of a window and will attract birds (but not squirrels) year round for perfect viewing. Don’t forget the birdseed. $60, uncommongoods.com —MK

Flowers for Dreams Subscription – Here’s a chance to brighten someone’s day while doing some good. Flowers for Dreams sends gorgeous flowers and plants, while donating 25% of its net profits to local charities. They offer two subscription plans, one delivers a complete bouquet, while the DIY subscription sends a loose bundle of blooms, a set of tools and a mason jar with the first delivery, and video instructions on how to make your florals into a beautiful arrangement. $35-$70 per delivery, flowersfordreams.com —LH

Bananagrams – You can play lots of games online with friends, but it feels more personal to open a video chat, take out physical copies of the same game and let the competition rip. My family has always liked Bananagrams (sort of a free-form version of Scrabble). Giving joint games is an incentive to schedule a regular game time, which is what a lonely heart will probably love the most. $15, bananagrams.com —LH

Stuck in Place

It’s dreary out (at least in the northern half of the country) and the temptation to hibernate is real, but if you’ve got a person on your list who wants to keep (or get moving) here are our ideas.

Warm Mittens – Do you know that Norwegian saying: There’s no bad weather, only bad clothes? Since moving to Chicago, I’ve embraced it and my favorite gift—since my hands are always cold—are these mittens by Laurentian, which have saved my winter walks. They’re made in Canada from sheepskin-lined leather and they’re much chicer than my ski mittens. $134, Moccasins Canada —LH

Audiobooks – A subscription to an audiobook site and a nice set of headphones, is a winning combo for encouraging movement. You’re feeding your brain and exercising your body all at the same time: efficiency! My fave headphones are my AirPod Pros. $250, plus subscription, apple.com, libro.fm (which supports independent bookstores) —LH

Wear Around Weights – As we learned from our Get Strong Challenge, doing even a few minutes of strength training makes a big difference. These colorful Bala Bangles come in one or two-pound weights, and are worn on your wrists or ankles to add a little resistance to anything you do. $49, shopbala.com —MK

Water Resistant Fanny Pack – A “hip” neoprene hands-free bag will encourage any couch potato to stride out into the elements with confidence, knowing their essentials are handy and secure. It can be worn as a crossbody bag as well. $85, dagnedover.com —MK

House Surfer

We know a lot of twenty-somethings who can work from anywhere so they’ve given up their expensive city apartment leases. While they bop between their parents’ place, friends’ pads and warm-weather rentals, here are some easy-pack gifts that will make them feel at home wherever they roam.

Packing Cubes – When living out of a suitcase, a good quality set of packing cubes is essential. This lightweight Clarity Packing Cube Trio comes in a variety of colors and is sure to help your traveler stay neat and organized. $65, Truffleco.com —MK

Portable Monitor – House surfers earn their living on the go, and squinting at a little laptop screen all day is a pain. This top-rated LePow 15.6 inch monitor provides much needed screen space for work or entertainment and connects to a phone, laptop or gaming system, $140, amazon.com —MK

Patagonia Black Hole Pack – As the mom of three twenty-somethings who have moved a lot this past year, Patagonia is high on their lists for its social activism, great looks and practical hauling ability. The Black Hole Packs, in particular, are essential if you’re desk surfing, couch surfing or otherwise in transit. $79-$149, patagonia.comLH

Olive and June Manicure Kit – I miss regular manicures and pedicures, and if you’re on the move, you probably also miss the regular meeting time with friends and familiar salon. These kits make it much easier to give yourself pro-looking nails with special handles on the brushes so you can paint both left and right hands without getting polish all over your cuticles. Very clever! $80, oliveandjune.comLH

Screen Queen

New hobbies are in demand for every age category, so here are a few that we think might work to for a loved one who’s desperate for a new past time.

Art Class – The upside of a virtual class is that it’s a low-pressure and supportive way to explore a new pursuit. Lillstreet Art Center in Ravenswood has adapted to the times and has virtual beginner classes. From photo editing to frame loom weaving to knitting, you’ll find something to spark your friend’s creative side. $165, Lillstreet Art CenterLH

Cooking Class – This class is specific to Chicago, since you pick up the food at the restaurant then get a link to cook one dish with the chef (the appetizers and dessert come ready made). It’s a fun way to up your cooking skills with Thai Dang co-owner of HaiSous Vietnamese Kitchen in Pilsen. If you’re buying for someone elsewhere, a little googling should find something similar near your giftee. It’s a perfect gift for a couple who are new to cooking and miss traveling to exotic locations. $40 per person with a two person minimum, HaiSous Vietnamese KitchenLH

Ukulele – These compact, affordable instruments are easy to learn to play—it only takes about 3-6 months of practice to play songs fairly well. For a music-loving friend who’s ready to try their hand at a new skill, a ukulele may hit the perfect note. $100, guitarcenter.com —MK

Backgammon Set – Enliven a couple’s evenings at home with some old school, face-to-face competition. The game gets a modern twist with an arty backgammon set from New York’s MoMA store. $95, store.moma.org —MK

Has it All

You know the guy (or gal). They really do have everything, including intimidatingly good taste. No need to worry about messing up their aesthetic with these thoughtful treats—they deliver big pleasure while taking up little space.

David Sedaris Audiobook – Sedaris’ new book The Best of Me is a hilarious read, but perhaps an even better listen. The irreverent author narrates his funniest stories and essays. $40, thebookstall.com —MK

Jam it Up – American Spoon is a Northern Michigan company that makes delicious preserves and condiments in small batches. The Favorite Preserves Trio includes Red Haven Peach, Early Glow Strawberry and Sour Cherry preserves. A yummy way to start the day. Spoon.com, $37 —MK

Equilibria Gift Pack – The nicest gift this year might be something that helps us calm down and sleep! Equilibria is a woman-owned CBD apothecary (legal everywhere) that includes a one-on-one virtual consultation with every product. The Joy of Sleep is probably a great starting point for someone curious about CBD. $129, myeq.comLH

Bath and Shower Bombs – Relaxing in a tub with a moisturizing or invigorating bath bomb is a treat, but for those (crazy?) souls who hate baths or who don’t have a tub (sorry!), Lush makes shower bombs that are almost as much fun. If you’re looking for a higher-end gift, these make great additions to a self-care basket—just add a luxury candle, moisturizer and exfoliating brush. Heaven! $4-$9, lushusa.comLH

Appreciated One

From stocking stuffers to book club virtual gift exchanges, we all have people we want to send a little something, but wouldn’t it be nice to just buy everyone the same thing? It’s not lazy, honest! It’s really genius. And make sure you order a few extra, because you’ll for sure forget someone, and if you end up with one extra, then you can throw it in your stocking. Win!

Pillow Spray – A genius product that can be sprayed on a pillow for a whiff of its citrus and cedar scent, but it’s also antimicrobial, germicidal and insect repelling, so in a pinch it’ll clean your hands and keep mosquitos away—who couldn’t use this spray. $18, East ForkLH

Chocolate Bars – The chocolate-obsessed crew at Cocoa & Co. will pull together a trio of handcrafted chocolate bars for you. All you have to specify is dark, milk or mixed and they’ll do the rest. $25, Cocoa & Co.LH

Bubbly Wrapped – Tis the season for toasting and a bottle of Veuve Cliquot Champagne is always a luxury, but this one is extra fun packaged in a reusable retro cassette tape gift box. $45, Binnys.com —MK

Candle/Planter Kit – Who wouldn’t love this clever Modern Sprout “Glow and Grow” vessel that transforms from candle to flower pot once the wax is used up? Seeds and planting material included. $35, urbanoutfitters.com —MK

NOTE: These picks are all editorial and at this time we do not use affiliate links.

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