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Perfect Holiday Gifts for Impossible People

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Holiday Gift Guide: What to Get That IMPOSSIBLE PERSON on Your List

HolidayGiftGuide_GMAG_WebHoliday shopping is hard enough without trying to find that perfect gift for the more challenging people on your list. What do you get the not-your-biggest-fan mother-in-law? Or the crazy-aunt-from-up-north? Or the father-who-has-everything? Lucky for you, our hours of scouring the Internet for unique gifts includes everyone on your list – even the craziest of your clan! They may not hit a grand slam, but they will at least earn you an A for effort, therefore maintaining your status as everyone”s favorite – well, almost everyone”s.

Crazy Aunt/Uncle
Ah, the crazy aunt/uncle from up North, or down South, or maybe you aren”t exactly sure where they live. Most of us have at least one, and aren”t sure how to honor them during the holidays. Why not accentuate what makes them individuals by aiding their pursuit of unusual interests like knitting, NASCAR, hunting or doomsday prepping? Consider an outfit for one of their many pets, a book on current conspiracy theories, or a snuggie featuring their favorite NFL team. If you prefer a less subtle approach, many websites, including CafePress.com, have a full line of products dedicated to the “Crazy Aunt”.

Saintly Grandmother
When your sweet, saintly grandmother hands you the annual glittering card and five bucks this Christmas, how will you respond? Sentimental gifts are always a good bet, so design a custom Christmas ornament or photo book from Shutterfly, complete with photos from a recent family vacation. Accompany these gifts with handmade treasures from the grandkids or great-grandkids, and you”re good as gold for another year.

The Extreme Animal Lover
This one seems challenging, but is actually pretty simple. Just find something that reinforces how horrible people are compared to animals. For example, car bumper stickers declaring that their dog is “smarter than your honor student” or some recycled stationery featuring endangered species of various kinds are safe bets, as is making a donation in their honor to a local rescue or the ASPCA. You can even adopt a tiger in their honor via the World Wildlife Fund.

Perpetually Satisfied or Dissatisfied Father
What do you get the man who has everything? Or the one who always finds a problem with your hard-thought and over-analyzed gifts? Uncommon Goods has fantastic options for dads who are hard to please; you can choose a framed blueprint of his favorite ballpark, a personalized whiskey barrel, a ninja umbrella, or wooden beer tote complete with bottle opener. For the dad who lives in the kitchen or at the grill, try the weiner dog oil and vinegar set, or the salts of the world sampler. For most, a rare bottle of wine or a well-aged scotch will do the trick, while helping everyone survive the holidays.

Underachieving/Overachieving Sibling
Many of us are plagued with a family underachiever – whether a sibling, cousin or in-law – who, despite their lack of accomplishment, seem to ease through life and challenge you for family favorite. Find a gift that celebrates their irresponsibility while simultaneously allowing you to make a statement. Perhaps something from your college gift store might remind them that attending college is a good idea. Take it one step further by purchasing them a college course from The Great Courses to kick start them down the road to self improvement.

If you don”t have an underachieving sibling, there”s a good chance you have the opposite: the overachieving sibling. What gift could possibly impress them while they woo the family with tales of their latest Nobel Peace Prize? Go with something pretentious: imported organic (fair trade) tea, a book of poems from an ambiguously under-celebrated author, or a Jackson Pollack coffee table book, all of which you could find at Barnes and Noble. You can inevitably ensure their standing as the ultimate go-getter by purchasing an acre of land on planet Mars!

Not-Your-Fan Mother-in-Law
An all too familiar scenario during the holidays: you”re visiting the in-laws, whose naughty list you always seem to be on, and you don”t want to make it worse by failing with the all-important gift.

Accentuate the positive by finding a gift that celebrates her son, such as an electronic picture frame pre-loaded with photos of him being the world”s best dad or little league coach, etc. Try to warm her heart with a nice throw blanket or home accessory from Pottery Barn or West Elm; provide music to her ears with tickets to the symphony or an upcoming traveling Broadway show. French Graffiti, a local company, offers a wide variety of hand-made, Paris-inspired kitchen towels, scarves and prints that would make any suburban woman feel exotic. All it takes is a short trip to Francesca”s Boutiques!

For the brave, consider a meat tenderizer from Williams Sonoma, whose reputation proves you spare no expense. This will allow her to simultaneously release her frustrations while appreciating your thoughtfulness. It would also support her belief that she is a better cook than you.

The Bratty Niece/Nephew or Goth/Emo/Name-Your-Issue Teenager
What do you do for that niece or nephew you”re already dreading seeing, or more to the point, hearing about? A subtle approach for unruly tykes would be purchasing gifts that blatantly point out the problems their parents should be working to fix, such as shirts that proclaim “I”m a Princess and What I Say Goes!” or “I Learned it all from my Daddy” or “Mine, mine, mine!”

Fast forward a few years and contemplate the tween or teen in your life. Certainly a tricky age, because you don”t want to run the risk of looking even less relevant than they already find you. Definitely think Apple store, and choose from a huge selection of iPad and iPhone cases and accessories. iTunes gift cards provide multiuser coverage for their much-beloved, yet obscure music tastes and app-addictions. Sites like Red Bubble have thousands of items designed for counter-culture fans, such as World of Warcraft, Supernatural and anime t-shirts. Stay away from gifts that pretend to be counter-culture, such as the Twilight trilogy – that would only ensure that you aren”t as cool as they knew you weren”t.