The Gift-Givers Guide to Overthinking Literally Everything
By: Jamie Siebens
Tags: Humor, Mental Health, Satire, Relationships, Self Improvement

The Gift-Givers Guide to Overthinking Literally Everything

Lessons from a pro.

Photo by Angèle Kamp on Unsplash

Are gift cards tacky and impersonal? I ask myself this question every holiday shopping season.

Which is worse: Getting someone something that they hate and feel obliged to wear or use? Or handing them an envelope with a card that says “I don’t know you well enough to choose an appropriate gift. I hope you like Sephora.”

If you think this kind of internal dialogue is inane, if you’ve not spent more than five minutes in your lifetime considering the social and moral consequences of gifting a gift card, if the thought of shopping for holiday presents fills you with joy and not anxiety,

You should know: There’s another way.

Overthinking literally everything about gift giving doesn’t come naturally to everyone, but like many other things it’s a skill that can be learned. Fortunately for you, this guide covers all the basics and will have you second guessing everything you’ve ever thought about giving in no time.

How to Slowly Drive Yourself to The Brink of Insanity While You Attempt Small But Meaningful Acts of Generosity — A Beginners Guide

Alternate Title: How to Suck All the Fun Out of Gifting.

If one or two of the following already applies to you, you’re in luck! Waffling and second-guessing yourself is probably already second nature. All you need is a little shove to push you over the edge into complete analysis paralysis.

But if you want to really excel at overthinking, you need to:

1. Be responsible for — literally anything — besides gift giving.

Like holding down a job, caring for small humans, or making sure everyone in your household eats, showers, and has clean laundry. Apparently these responsibilities are meaningful and rewarding in their own right, but they’re also perfect for complicating even the simplest gifting task.

2. Be concerned about the environment.

If you’ve given the environment more than a passing thought, the idea of buying even one more thing that’s going to end up in a thrift store or landfill will make you cringe. Even better, when you see the 12-pack of shrink-wrapped mystery dolls on your niece’s wish list — basically a million pieces of micro-plastic just waiting to happen — you’ll die a little bit inside. Lather. Rinse. Repeat.

3. Have a strict budget you actually need to follow.

The deep certainty that overspending on gifts means you won’t be able to make rent or buy groceries will really dial up the mental calisthenics. This also applies when you have a shopping list that’s bigger than your budget. If shopping for presents requires more math than your tax return, you’re well on your way to second-guessing, and third-guessing, and fourth-guessing every item on your list.

4. Really care about shopping local and/or shopping small.

This is important. But you can’t just sort of care, you need to really care. You might not have the time or budget to shop small, but you know you should. And when you know better, you do better. Or, at the very least, you feel extremely guilty for every big box purchase you make.

5. Feel weird about any of the following:

Gifting chocolates, cookies, hard cheeses, or cured meat — Because saturated fat and diabetes might not be the perfect thing to give.

— Because saturated fat and diabetes might not be the perfect thing to give. Gifting house plants or other living things — Is this too much pressure? What if they’re allergic? What if it dies?

— Is this too much pressure? What if they’re allergic? What if it dies? Gifting restaurant or spa gift certificates — Typically expensive. You also don’t want to run the risk of paying for only half a meal or facial, which then is basically just giving a coupon for 50% off. Cringe.

— Typically expensive. You also don’t want to run the risk of paying for only half a meal or facial, which then is basically just giving a coupon for 50% off. Cringe. Gifting any sort of generic gift card — Nothing says deep and meaningful like a heartfelt gift of retail store credit.

— Nothing says deep and meaningful like a heartfelt gift of retail store credit. Gifting clothing or accessories — This is a test of how well do you really know this person that (literally) no one wants you to take.

— This is a test of how well do you really know this person that (literally) no one wants you to take. Gifting subscriptions or memberships — For some reason this feels like the ultimate copout. And again, how well do you know them, really?

If you fit all of the above, and still aren’t overthinking every miniscule gift giving gesture, there’s one thing that’s guaranteed to get you there.

You must believe that every gift should be magical and deeply meaningful.

Weighing each and every gift you give as if it is the most important present they’ll ever receive isn’t for amateurs. This is pro-level overthinking at its finest. Deep down, you know that this isn’t just a gift — it’s a metric that’s directly tied to your own sense of identity and self worth. Missing the mark in this area isn’t just a mistake, it’s an abomination.

Overthinking isn’t for the faint of heart.

Sure it’s easier to see gifting as a means to an end. Some people actually take pride in zipping through their list and making everyone’s dreams come true by simply getting them what they asked for, or a gift card, or cash.

But if you truly believe “It’s the thought that counts,” then there’s no better way to demonstrate your love than to investing every last ounce of your sanity into finding the perfect gift.

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