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The Holiday Struggle

8 Toughest People To Shop For Over The Holidays | Part I

Gift shopping is seriously hard! We’ve all been through the annoying ordeal. You’re really excited to give someone a gift, you struggle to choose the perfect present, you proudly give it to the recipient who is notoriously difficult to shop for, you watch them pretend to like it (”oh… you shouldn’t have”), then you immediately seize the gift from their ungrateful hands and burn it in front of them. Okay, maybe not that last part, but everything else.

Or worse, you’ve been on the other end—excited to get a gift from a close friend only to open the gift and realize the friend apparently has zero idea what you like (or has an idea and is trolling you). You’re not that difficult to shop for—that’s why we’re here. We have the best Holiday Gift Quiz of the season! But just in case you’re as helpless as Drake in a room full of exotic dancers when it comes to holiday shopping, we’ve got you covered with gift ideas for the 8 most difficult people to shop for this holiday season.


We know she made middle school years one embarrassing incident after another, after another and another (seriously why did she let you wear those side bangs), but this lady gave up wine for 9 months for you, so you better find something great. She more than deserves an amazing gift. I’m sure she’d love a Birkin, but we don’t all have Birkin money, so the thought is going to be what counts here.

While she might not want anything handmade anymore, she probably does want something one of a kind. Think artwork, a personalized photo book, some some chic jewelry, or that face oil she only treats herself to every once in awhile. And if she has a green thumb (or wishes she did!), give her this Indoor Grow Garden to help her make it through the winter months with some green.

Be grateful for this lady, you could have been born with a momager who negotiated the release of your sex tape and built you and your family into a media empire. Actually, that doesn’t sound so bad.

Get the : Spigo Indoor LED Light Grow Garden, Pearl White : Garden & Outdoor from Amazon for 57.99.


He’s probably one of two types of guy—the one who wants the newest Rolex or the one who doesn’t even know they come out with new Rolexes. But just in case you are $10,000 short (or whatever a Rolex costs), we have a couple of options for you. For Dad #1, go for one of these nice Old Fashioned set for a nice addition to his bar cart or this Smart Portable Speaker With Alexa. This might just give you some relief from his normal skipping records.

For Dad #2, go with this cool pasta maker or beer foamer.

Get the Menu | Beer Foamer | AHAlife from AHAlife for $74.

Best Friend

The Offset to your Quavo. Serena to your Blair. The Phoebe to your Jessica. You basically share everything already, so it’s in your best interest to buy her whatever it is of yours she feels a little too comfortable borrowing. That bag you forgot was yours, that Fenty highlighter she’s used 90% of, this mug that perfectly captures her spiritual beliefs, is or that shirt that’s claimed squatter’s rights in her closet.

Get the Killawatt Freestyle Highlighter - FENTY BEAUTY by Rihanna | Sephora from Sephora for $34.

Best Frenemy

Her. You pretend you love her. You love to hate her. But mostly she’s just as annoying as an overused Instagram caption (“Do it look like I was left off Bad and Boujee?” Yes. Yes it does). This gift will probably seem like a drag. It’s honestly just for appearances, so get something that’s both a gift and a dig. Maybe a framed picture of you and your new BAE since she’s still #partyofone. If that doesn’t work you can always give them a mug that matched their personality, perfume, or a candle. Anything that insinuates she stinks.

Get the Free Sass from Look Human for $19.

Check back next week for the next four people who are so difficult to gift shop for. In in the meantime, get your easy shopping done with the help of our gift guides.

The Holiday Struggle series was creative directed and edited by Emmy-nominated writer Damilare Sonoiki.

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