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The Best Gifts for the Impossible Man

Men can be particular, opinionated, or even obstinate when it comes to the things (read: objects and activities) they love. This is doubly true – for complex reasons that have to do with gender performance and neuroscience – for men in their 50s, 60s, and 70s, a pain-in-the-ass demographic of people incapable of receiving a gift with grace. They key to buying for these men is making a clever pivot. 

Don’t get them anything nice. For some reason, men tend to be the hardest group of people to shop for. (Sorry, men!) Over on the r/gifts subreddit, you can find thread after thread of people trying to source gifts for a very particular type of guy: a gamer, a toy shop owner, and a 60-year-old father-in-law. In-laws in general can be one of the hardest demographics to shop for, but they’re by no means the only impossible people to shop for. So when shopping for the impossible man, where do you even begin? For starters, don’t overthink it. 

“Sometimes, a really good gift isn’t something particularly sexy or exciting—it’s something practical,” says Dan Oshinsky, the impossible man who runs the newsletter consulting firm Inbox Collective. “It’s that thing you gave a friend that they use every day, and every time they do, they think of you.”

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Books, food, and all-around utilitarian items can make great gifts. Does he drink coffee? How about a travel carafe? Does he travel a lot for work? Filson bags aren’t original, but they are really, really well made timeless. Start with what your impossible man likes, what he does on a regular basis, and keep it simple. When in doubt, just go for something you think he needs. 

Still stumped? These selections should inspire a kick-ass gift for the man in your life who’s positively impossible to shop for. 

Courtesy of Crate & Barrel

$44.95

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“I love getting something both nice and practical, like this decanter from Crate & Barrel,” says St. Petersburg-based media consultant Jensyn Gagne. A decanter is something that the so-called impossible man probably wouldn’t buy for himself, and if he works out of an office, it’s a stylish accessory that will allow him to channel his inner Don Draper. 

Courtesy of Le Labo

$76.00

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Gagne, who married to a man she says can be challenging to shop for earlier this year, suggests this Le Labo lotion as well. Sure, you may be thinking that lotion is not a typical gift for a difficult dude, but flip that around: it’s something useful that they wouldn’t think of in a million years, and it will make for a surprising gift.

Courtesy of Meatworks

$119.00 – $249.00

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Unless he’s a vegetarian, a gift box from Meatworks will most likely thrill your impossible recipient, especially if he likes to grill. Butcher Box has a varied selection of meats and gift boxes to select from, including steak- and burger-centric bundles. And Meatworks’ offerings are of the highest quality, too—they say they only carry the top three percent of USDA prime beef. 

Courtesy of SpiceWalla

$59.99

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If we’re dealing with a guy who likes to grill and you’re looking for a lower price point, you might want to give him a selection of spices to season said meats. This collection from SpiceWalla comes with 10 different seasonings, including chili lime, Kansas City BBQ rub, lemon pepper, and many more. You, too, will reap the benefits. 

Courtesy of Uncommon Goods

$38.00 – $65.00

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Perhaps the dude in question fancies himself a mixologist. In that case, he absolutely needs one of these cocktail smokers. Men love to play with fire, and this little gadget allows him to make smoky cocktails in more of a contained environment. Besides, if a difficult man is opening gifts, there’s probably a good reason to drink. do you like cocktails? Giving him the gift of experimentation is a gift to you as well. 

Courtesy of Mouth

$80.50

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It’s a proven fact that men love snacks. “Specialty snacks are a great option,” says Portland-based creator Ashley Hosmer. “I always load up my husband’s stocking with new snacks, last year I got him Muddy Bites—they’re the tip of sundae cones as bite sized snacks.” Mouth is also a solid source for unique snacks, but if you’re coming up short there, look to an old faithful: Nuts.com.  

Courtesy of Best Buy

$149.99

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Hosmer says that her go-to move for gift giving is elevating an everyday item. So if the guy you have in mind already has headphones, no problem. Give him some nicer ones. These Beats headphones are a great bet. They’re noise canceling and wireless, and they’re great for traveling, commuting, or just independent listening. 

Courtesy of Son of a Tailor

$64.00

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T-shirts may seem simple, but simple is not a bad thing. “My husband wears a black t-shirt every day and is very particular about the fit,” says Hosmer. “Son of a Tailor makes customizable tees—great for the picky man in your life.” You can customize every element of the fit on  these shirts, so if your man is unsatisfied with his typical tees, these might be the right gift for him. 

Courtesy of Nordstrom

$71.50 $109.95 – $120.00

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If you’d describe the man you’re buying a gift for as remotely “difficult,” there’s a zero percent chance he’d ever buy himself nice slippers like these Uggs. And there’s also a 100 percent chance he’d love them. You could probably give Ugg slippers to anyone you need to buy a gift for and they’d be happy. The impossible man is no exception. 

Courtesy of Uncommon Goods

$85.00 – $185.00

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Do you have a sports fan on your hands? Uncommon Goods carries plenty of unconventional sports merchandise, including these stadium prints for every Major League Baseball stadium. If baseball is not his bag, don’t worry. They also carry books that tell the complete history of every single NFL team. 

Courtesy of Customize My Clubs

$15.00 – $40.00+

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So maybe the MLB or the NFL isn’t this guy’s cup of tea. Writer Drew Millard, whose book Golf Can Save Your Life is out next month, has a suggestion: “Send their wedges off to be ‘stamped.’ There are people out there who will use some sort of very hot metal thingamajig to imprint cool little designs and/or words and/or initials on someone’s golf clubs,” Millard says. “These people will then paint them, and it will look really neat.https://www.customizemyclubs.com/ Lots of pro golfers have stamped wedges, and while none of us will be a pro golfer, it is at least possible to give your golfing loved one the gift of pretending.” 

Courtesy of Uncommon Goods

$18.00

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It’s a proven fact: dudes love to go extremely deep on niche topics, and for a very particular dude, that includes cooking with cannabis. This cookbook will show them how to make their own gummies at home, and there may be some trial and error involved. But who doesn’t love a project that ends in elevating your mental state? 

Courtesy of Yeti

$20.00 – $38.00

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This is the kind of thing the impossible man could use every day. What he puts in it—coffee, beer, maybe a cocktail—is not our business. But it’s versatile, in that it works for all of the above. Give it to him with his favorite coffee (or alcohol) and he’ll be sure to love it.