The holiday season is here, and I’m once again very unprepared. If there’s one thing I absolutely dread, it’s shopping for family and friends. I’m an overthinker, and the mere thought of someone not enjoying their Christmas gift haunts me.
For starters, I have 11 cousins, two of whom have children. Ironically, it’s not the monetary aspect that stresses me out—it’s finding the perfect gift for everyone. Sure, the stress and holiday traffic are also major downfalls, but when in doubt, order online.
One year, we tried to make holiday shopping easier for everyone by doing Secret Santa as our sole gift exchange. It sounded great on paper, but it was a complete bust because my cousins complained about the people they got. It’s safe to say we never mention Christmas of 2014.
I used to be the person who would buy a card, slip in some cash or a gift card, and call it a day. But as I’ve grown older, I’ve started to appreciate the importance of curating gifts tailored to someone’s interests. I’ve also learned that gift cards are more vulnerable than ever to fraud, so we’ve reached the point where they’re basically off-limits.
Now, I try to pinpoint my friends’ and family’s interests down to a T. For some, it’s easy; for others—like my dad—it’s mission impossible. I’ve even asked him directly what he wants, and yet my gifts still end up being regifted. He may or may not still receive a card with money, but I have my reasons.
Lately, I’ve taken to having friends and family send me wish lists. Sure, it’s a 50/50 chance they’ll know what I’m getting them, but at least I know it’s something they’ll enjoy.
I like to categorize the people I shop for: the picky ones, who are hard to please, and the ones who never want anything at all. What exactly do you buy for the latter? My mother is one of those people, and it drives me insane. I know she’d be happy with a rock from outside, but I want to do better than that. So I pay close attention and try to notice the things she might actually enjoy.
Despite the stress, overthinking, and occasional gift-giving failures, there’s something deeply satisfying about finding the right gift for someone. It’s a little piece of joy you get to give, wrapped up in paper, ribbon, and thoughtfulness.

