Still Stumped on Holiday Gifts for Picky People? We Can Help

https://www.nytimes.com/2019/12/16/smarter-living/last-minute-gifts-hard-to-please.html

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We asked our readers to tell us about the hardest-to-please person on their holiday gift list. With time to shop running out, we hope these ideas can provide some inspiration. Questions have been edited for length and clarity.

(If you’re still stumped on what to give the tricky people on your own list, explore our gift guide or these gift ideas from our friends at Wirecutter.)

Q: The trickiest person on my holiday gift list has to be my father. He has interests (including the Seattle Seahawks), but immediately buys himself anything he wants and doesn’t like knickknacks or superfluous things. My budget is less than $100; less than $50 is even better.

A: You might try tracking down a Seahawks shirt or jersey with the name of a player from the team’s earlier heyday (this Steve Largent jersey is a good option), or other vintage Seahawks gear. Several of my colleagues have gifted vintage merchandise to the hard-to-please sports fans in their own families, and they’ve universally been a hit. — Wirecutter staff

My dad is 93. He is still in great form and sound of mind and lacks nothing. He has everything he wants; “if I want it, I would have bought it,” he says. Once I found one of his favorite books from childhood: He loved it. Next year I tried the same thing — an old book in German. He told me it gave him nightmares as a child and to please take it back. What do you buy for an old man who has everything he wants and needs nothing?

If a book was one of your most successful gifts, why not consider an audiobook subscription? I did this for my mom, who protested she would never use it but now listens to books (often ones she would not have otherwise read) while she cleans and cooks and putters around the house. The audiobook field is booming and quality has never been higher, not just when it comes to new books, but classics, too. There are plenty of services — including Scribd, Audible, Kobo, Downpour and Libro.fm — at a variety of price points. — Tina Jordan, deputy editor, The New York Times Book Review

My dad is a very smart guy. Likes new technology, but typically buys what he wants for himself after analyzing each option to death. He reads a lot; sci-fi, fantasy or nonfiction mostly, I think. They’re always e-books so I don’t know what he is reading. He plays Settlers of Catan a TON while he is home with my mom, and enjoys other board games too. And he plays Civilization with his sister via email. He works remotely half the time and spends half his time away from home.

Since he likes Catan, he may enjoy one of the newer strategy games for adults — perhaps the civilization-building game 7 Wonders, which is competitive but also fun for just two players (it’s more entertaining with a group). If you think he is due for an e-reader upgrade, he might like a Kindle Paperwhite. And because he works in multiple places, he would likely appreciate a portable power bank; go with the Jackery Bolt, which will charge most smartphones twice and fits in a pocket, so he’ll never end up with a dead device while he is on the go. — Wirecutter staff

My dad likes music, beer, dark chocolate, fancy herbal and medicinal teas, being outside and anything spicy. He dislikes things that are sentimental or cheesy (other than to make fun of them) and hates ties. The music-related equipment he likes is usually out of my budget ($50 to $100), and we usually settle on a new pair of jeans and a flannel shirt for him. I would love to get him something more meaningful this year!

I prefer giving edible gifts because it means less stuff the recipient has to store. (Can you tell I’ve lived in New York City for 20 years?) I’m a big fan of Dandelion Chocolates in San Francisco, so if you want to go the chocolate route, a nice three-bar set and a hot chocolate mix would likely make him happy, and you would still be under budget. If he is a Nina Simone fan, this classic-style gym sweatshirt from Nature is an Object is a hip yet dad-friendly replacement for the annual flannel. Toss in a Zippo handwarmer (or two) for chilly hikes. — Margaux Laskey, Senior Staff Editor, NYT Cooking

My father-in-law, who is in his 80s, is an active, no-frills guy. He is also a true handyman and always tinkers with stuff on his own. He built and renovated his entire house, fixes old lawn mowers and sells them, does all his own car work and loves to fish When he visits my house in the suburbs, he gets antsy just sitting around for too long. My budget is $150.

Since he likes to tinker and fix stuff, he might like new wrenches, a good pocketknife or a great flashlight. Even if he already has these items, he’ll probably be pleased to have extras that he can use wherever he is at — on his boat, in the garage or at your place. Next time he comes to visit, put him to work with these new tools to ease his restlessness. — Wirecutter staff

My mom is impossible to shop for. She loves being a grandma to my 2-year-old niece but she has all the goodies at the house to spoil her. I’ve gotten her movie gift cards with promises of “brunch and a movie” quality time but we’re both so busy that we rarely make the time to do it. My dream is to one day get her, my dad, brother, sister-in-law and niece an all-inclusive vacation somewhere where she doesn’t have to cook or clean and can just relax with us. No money for that though. Help!

What if you didn’t have to travel and could still offer her — and the rest of your family — a vacation? A pass from ResortPass (prices start at $15) grants daily access to more than 170 luxury hotels all over the country, allowing users to enjoy gorgeous five-star pools and spas without having to pay for a hotel room. But you mentioned time is a perennial problem, so perhaps consider a subscription to Little Passports for your mom to enjoy with your niece. Each month a new kit about a new country and its culture arrives, with fun activities and stories in each box. My kid loves it. — Elisabeth Goodridge, deputy editor, Travel

My mom is elderly but vital. She is widowed, and has plenty of money to live on. She needs nothing, is soon moving so doesn’t want a lot more “stuff” and has expensive, sometimes finicky taste. I feel as if I have tried everything under the sun to avoid giving her more clutter. I’m not looking for the perfect gift, I just need some things for her to open so she isn’t left out.

My grandfather has one request for the holidays every year: That we bake him a batch of his mother’s poppy seed cookies. He is similarly tricky to buy for, and not really in need of more “stuff” — but these hit a certain sentimental spot that he really enjoys. If there’s an old family recipe that you remember making with your mom, something homemade — maybe with a note about why it’s special for you — could go a long way. If you want to add something more permanent, deliver them in a special dish or tin that she can keep. And if nothing comes to mind recipe-wise, start a new cooking or baking tradition of your own: Singular experiences may not be a hit, but try something like a cooking class that you can do together — and bring the grandkids along. — Nancy Coleman, reporter fellow, Culture

My husband is the trickiest person on my list. He likes money, scoring deals to save money, and he’ll watch any sport on TV (except golf). He drives A LOT and spends 100 nights a year at hotels for his job. He likes beach vacations and money. Did I mention money? He is unsentimental and often my gifts get returned or go unused. My budget is about $400 to $500. Somebody has to help me. Even his mother hates buying him gifts.

For a man who values his money, why not give him something elegant to hold his precious bank notes? A Tiffany & Co. sterling silver money clip or a Louis Vuitton wallet (which can be monogrammed for an extra special touch) are two good options. Alternately, consider something comfortable for him to lounge in either while he is on the couch watching his favorite sports team or in the car driving on his next work trip. Sunspel makes quality cotton sweatpants and hoodies, or opt for something made from a finer material, like Nadaam’s cashmere sets. — Alex Tudela, market editor, T Magazine

My future mother-in-law, who lives in Houston, is a lovely, kind and caring person. She seems to enjoy coffee, sports (especially volleyball and football) and she loves her grandchildren — and sometimes wine! My budget is $50.

If she lives in Texas, she probably likes monograms (I’m from the South, so I feel like I’m qualified to say that), so what about a monogrammed Yeti coffee mug or tumbler in her favorite team colors? For something a bit more personal, get your hands on a really sweet photo of her and your soon-to-be-spouse as a child, scan it, upload it and get it framed by Framebridge. Cue the tears. — Margaux Laskey, Senior Staff Editor, NYT Cooking

My mother-in-law is in her mid-70s and lives in a one-bedroom apartment on the Upper East Side of Manhattan with her Chihuahua. She always buys herself whatever she wants and will not hesitate to pass on our gifts if they are not up her alley! The only thing we have ever gotten her that she loved was photos of her grandchildren, but we would like to delight her with something different!

This woman is my hero! A Chihuahua owns me as well — might I suggest shopping for the dog instead? A cashmere sweater, a self-heating bed, a blingy personalized collar? Or, since you know she loved photos of her grandchildren, how about a “fetching” professional photograph of her dog? I’ve been gifted a gorgeous, hand-drawn custom portrait of my misanthropic Chihuahua, and I love it. — Dodai Stewart, deputy editor, Metro

My husband is a recently retired television executive. He loves gadgets but has no use for tchotchkes — it has to be truly useful.

If your husband doesn’t already have a weather station, this is just the type of useful gadget he might like (we like one from Netatmo). It’ll measure the conditions outside your door, which can help him garden (say, to check if he needs to cover tomatoes from frost). He would probably also like an interesting plant from a native or heirloom nursery in your region. For instance, one of our editors gifted her mother-in-law, who lives in the Northeast, a pawpaw tree that is now bearing mango-like fruits. Throw in a plant history book for good measure. — Wirecutter staff

My father loves books but always complains he doesn’t have the time to read (and doesn’t like audiobooks). He has gotten a small reputation in our family for never taking presents out of the bag they were given to him in, so clearly we’ve all been striking out for years.

If your dad is a politics junkie, he might like one of the better books on politics or history published this year. My favorite was Patrick Radden Keefe’s “Say Nothing,” which tells the story of the Troubles in Northern Ireland through the prism of a 1972 murder in Belfast. It’s such a fast, page-turning read that it feels like a novel — but every word is true. — Tina Jordan, deputy editor, The New York Times Book Review

My significant other has all of the nice clothes he needs (and dresses very well), has every tech advance known to man, likes to cook (but we both have tiny apartments with little space) and read. I want to give an experience, but think cooking classes in New York are overrated. Stumped on the typical man who has everything issue.

The travel industry is all about “experiences” these days, and many a tour operator from here to Melbourne would be more than happy to design a personalized excursion or perhaps already offers one that would be appealing to your man. But I’m guessing you’re working with a budget, so: Locally (and plugging my favorite news media company), The Times has inspired city tours in Brooklyn and Greenwich Village, run by Urban Adventures and operated daily. If perhaps your significant other wants to get away and likes a hint of mystery, let a “surprise travel” tour operator take over. After you provide some basic information, these travel agencies plan your trip for you, disclosing your destination, lodging and other information at the last minute. (Available to budget travelers too.) — Elisabeth Goodridge, deputy editor, Travel

My husband is 72 years old and still working as a tax lawyer. He has absolutely no hobbies and has a difficult time walking. He loves to watch sports, especially basketball. His idea of a good day is sitting in front of the TV watching sports.

Help this man lean into the lounge lifestyle he craves. Crisp white pajamas or a velvet smoking jacket, perhaps? — Dodai Stewart, deputy editor, Metro

Every year, my husband is the toughest person on my list. He has very distinct likes and hobbies — watching sports, gaming and other tech, and is a cocktail enthusiast — but is an early adopter and buys himself whatever he wants as it becomes available. How do I get ahead of the guy who has everything but still make it interesting and useful? Budget up to $1,000.

A cocktail enthusiast should have top-notch equipment for making the drink of his choice. Lorenzi Milano transforms raw materials like horn, bamboo and mother-of-pearl into special, unique products for everyday use — like cocktail shakers and bottle openers, which would be handsome additions to any at-home bar. For something tech-related that isn’t just a gadget that he might already own, go for a fashionable case. Brands like Dior, Berluti and Bottega Veneta, for example, make fancy leather key-chain holsters for the ever-popular Apple AirPods. — Alex Tudela, market editor, T Magazine

My wife is tricky to buy for. After 16 years together, I still struggle. When I ask she says, “I don’t need anything.” Given that she is a rock star at work and the rock of our family, I want to buy her something that shows how important she is. Among her interests: reading.

If she likes to read, then give her some big, wonderful novels she can lose herself in, like Ann Patchett’s “The Dutch House” — a rich, old-fashioned family saga — or Jennifer Weiner’s “Mrs. Everything,” the story of the women’s movement told through the lives of two sisters raised in 1950s Detroit. There is also Kevin Wilson’s spiky, darkly funny “Nothing to See Here,” a tale of old friends and 10-year-old twins who burst into flames when they’re anxious or upset. (I know, I know: It sounds weird. But trust me.) — Tina Jordan, deputy editor, The New York Times Book Review

What presents do you suggest for Hanukkah, especially for children?

I have interfaith children and the types of gifts we give them aren’t different for Christmas and Hanukkah — but the size might be. For the eight nights of Hanukkah we give them smaller gifts — the equivalent of stocking stuffers on Christmas. Depending on the age or gender of the child, some suggestions: kid-friendly nail polish like Piggy Paint, scrunchies — Claire’s has a plethora, Calico Critters (small dolls), Transformers. — Jessica Grose, lead editor, Parenting

My father-in-law cares a lot about appearance and likes nice things, but our budget is $50 currently. Help! He is currently retired, enjoys his boat and is constantly finding tasks to do to keep himself busy. He has enjoyed our practical gifts in the past, but a man can only have so many coolers.

A practical man who wants to keep his face looking fresh after spending hours out on the water needs a good hat. Consider one of these sun hats, and throw in some sunscreen for good measure. — Lauren Reddy, audience director, Special Projects.