The Best Holiday Gifts For The Challenging People On Your List 

We all know those people who are just a challenge to find holiday gifts — they either insist they don’t want or need anything, or perhaps they simply have very discerning tastes. Either way, if you want to treat them to a little something around the holidays (or whenever) it can be difficult to pick out something that they’ll love and actually use. So here are some of the best holiday gifts for the challenging people on your list.

Best Holiday 2023 Gifts For The Challenging

best holiday gifts for the hard to buy for fountainof30

Media Subscriptions

While not a physical gift, a year of Max, Netflix, or Paramount+ (or the streamer of their choice) might be extremely appreciated. Things like Audible subscriptions if they enjoy audiobooks, Spotify, or newspaper or digital magazine subscriptions (or even paper editions if they are old school) can be great options as well. 


* indicates required

Couch Trays

This is such a simple thing that could easily be paired with the aforementioned subscription options, since having a convenient tray like this one from Amazon that fits over the arm of your couch definitely elevates a movie night. It even comes in multiple colors! 

Makeup Brushes or Travel Kits

These can come at nearly any price point, but a little set of makeup brushes (with decent tweezers) or similar travel-size kits can be a great gift if your recipient is a road warrior, or even just has a big trip coming up! This rose gold set from Amazon is under $10 and makes an excellent stocking stuffer. 

Jewelry Cleaner

They’ll be surprised at how much more sparkle their favorite pieces will have after a spin in a sonic jewelry cleaner. You can also clean eyeglasses in this one from Magnasonic

Nightstand Carafe

This might be the most elegant way to keep a glass of water near the bed (or anywhere else). We love the deep cobalt blue shade of this carafe and glass set from Maison Balzac

High Quality Audio

Even if your giftee has airpods or nice headphones already, a backup pair is always handy. Beats come in plenty of colors (we like the rose gold) and they might be more comfortable than earbuds.

Fancy Playing Cards or Board Games

Does your recipient love any card games or board games? A beautifully designed deck of cards like the Madrid playing cards from Jonathan Adler wouldn’t go amiss. Or if they are obsessed with Wordle, get them the board game version! 

If none of the above fit the bill, consider upgrading something your friend or family member uses everyday, like a nicer version of their ordinary go-to item. Get them something that’s useful but unexpectedly luxurious. Or maybe something they wouldn’t splurge on themselves but end up being surprised at how much they love it.

Shop The Best Holiday Gifts For The Challenging

Pictured above from left to right:

Subscriptions to Max, Netflix, Paramount+ or Audible

SINWANT Bamboo Sofa Clip on Side Table for Wide Couches Arm, Foldable Couch Tray, $32.99

Makeup Brushes BS-MALL, $9.99

Magnasonic Professional Ultrasonic Jewelry Cleaner with Digital Timer, $39.99

Maison Balzac J’ai Soif Carafe & Glasss | Indigo, $59

Beats Solo³ Bluetooth Wireless On-Ear Headphones, $99.99

Johnathan Adler Madrid Lacquer Card Set, $98

Wordle The Party Games, $18.59

What are your favorite items to give, and what are some of the most affordable or useful (but luxurious or surprising) gifts that you’ve gotten over the years? Let us know in the comments or share in our Growing Younger Facebook group!

–Jacqueline Zenn

You may also like to read Sweater Season: The Knits That Look Chic Right Now and Holiday 2023 Gift Guide: What To Give The New Mom In Your Life

This post contains affiliate links which may give us a commission at no additional cost to you.

Are you following Fountain Of 30 on FacebookTwitterInstagram and Pinterest? We’ve got lots going on, so join in on the fun! Subscribe to our newsletter here.  You don’t want to miss a post and promise not to bug you to death. Join our Facebook Group called Growing Younger where women discuss everything good and bad about being over 50. Additionally Lauren hosts a bi-weekly podcast called Beauty is a Bitch! and an Instagram Live series called “Growing Younger Gabfest with Lauren.”

Please pin!

holiday gift ideas when you don't know what to buy fountainof30 holiday gift guide 2023 for the challenging fountainof30


Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.