A Guide To Finding The Perfect Christmas Gift For Everyone In Your Life (While Making Sure You Still Come Out On Top In The End)

how to find perfect christmas gift


With the holiday season in full force, people are walking around with an extra pep in their step as the anticipation for Christmas builds up with each night they spend drinking hot chocolate out of festive mugs while splitting their attention between a Christmas movie they’ve seen dozens of times and the phone they’re using to browse the internet looking for gifts.`

I’m sure there are people out there who genuinely enjoy finding presents for others because they’re filled with the spirit of Christmas but I think even the most selfless of us are partially motivated to buy shit for other people because we know we’re going to get something in return. It might be the “Season of Giving” but the “receiving” part is really where it’s at.

It’s worth noting this doesn’t apply to you if you’re insanely rich; if you’re a famous YouTube star who can afford anything you could ever want, you’ll probably feel pretty good about using some of your fortune to buy a homeless guy a Tesla (and even better when those sweet, sweet views start pouring in). However, if you’re just a peasant like myself, you take a more calculated approach when it comes to deciding what to get by making sure you don’t spend more on others than you expect to receive in return.

That’s the real reason people can’t wait for December 25th to roll around: getting something that justifies all of the time and effort you would’ve preferred to avoid exerting over the past few weeks. Do you really think your curmudgeonly neighbor is nicer around this time of year because he threw a few more dollars than usual into the collection at church? Of course not! He’s counting down the days until his grandkids come over to give him the gift of the company he’s been craving for the past 364 days and they’ll pretend they’re happy to see him in exchange for the presents that await them.

I’m not saying giving doesn’t give me any joy; knowing someone genuinely appreciates something is a great feeling. However, it’s also incredibly fleeting. Was it nice to know my mom cried when I surprised my parents by calling the restaurant where they recently celebrated their anniversary and picking up the check? Obviously. Do you know what would’ve felt better? If she told me I didn’t have to do that and offered to pay me back, which I would’ve happily agreed to because I had no idea they were going to order two bottles of wine.

If you think I’m being too cynical or missing the point of what the holiday really means, then riddle me this: Why is everyone suddenly so generous around this time of year? If you really love giving so much, why would you wait until the last week of December to give your sibling a nice wool beanie when it’s been cold enough to wear once since Thanksgiving? Where the hell is all of this altruism during the other eleven months of the year? Is it because I’m…right? Yes, yes it is.

As I already alluded to, nothing ruins Christmas like taking stock of your piles of presents and realizing you’ve taken a net loss. If you want to avoid that fate, you have to employ a bit of strategy while shopping for others to ensure you’ll come out ahead by the time that the last gift is unwrapped. It might sound cold and materialistic, but I can’t think of two words that do a better job summing up this entire season.

This is obviously easier said than done, as finding the perfect gift for everyone with those restrictions in mind can be a brutal undertaking. When I say “perfect,” I’m not talking about something that’s going to leave someone speechless; you want to find something that makes other people think you thought about them even though you’re really thinking more about yourself.

There are a number of factors to take into consideration here, like the price, the importance the recipient plays in your life, and how much effort you think they’re going to put into what they’re going to give you. If the nerds behind the algorithms that dictate almost every facet of modern life were as smart as they’d like you to think, there would be an app you could use to find the ideal present for everyone in your life, but they’re apparently too busy wasting time on trivial endeavors like “space exploration” and “creating A.I. that could eventually enslave humanity” to focus on things with actual utility.

However, I’ve been playing this game for long enough to know a thing or two about how to win it. As a result, I’ve decided to share some of my knowledge and put together a handy guide concerning the best way to find something for the various groups of people you probably feel obligated to shop for. The best part? I’m not even expecting anything in return (but if you want to ask me for my Venmo, I’d be happy to help you out).


This group is a bit unique compared to the others on this list, as it should go without saying that buying something for everyone you work with is a terrible idea; not only will everyone think you’re a psychopath, you’ll also be digging yourself a hole that’s impossible to escape from based on the losses you’ll never come close to recouping.

The primary focus of this section is how to deal with the various gift exchanges you’ll encounter around Christmas, as more “traditional” presents are exclusively reserved for:

  1. People you like enough to actually interact with outside of work
  2. People you don’t really like who might get you something because you’re too good at pretending you like them
  3. People with the power to promote or fire you

That’s it.

There’s also nothing more vital than having a grasp on the company culture, as there are some things that would be a huge hit at places with weekly happy hours and an almost nonexistent dress code that wouldn’t fly at a prestigious law firm. I mean, I guess you could get a 73-year-old partner a shot glass with the words “I Love To Swallow” on it but he probably won’t find it as funny as you do.

If you find yourself participating in a Yankee Swap or White Elephant, you should consider yourself lucky, as it’s one the rare gift-giving scenarios where one of the best things you can do is track down the most inoffensive item you can think of; something that would make a friend or family member feel genuinely hurt if they received it because it’s so generic and devoid of thought, like a white coffee mug or an unscented candle.

Secret Santa is a bit trickier, as it can be tough to get a read on what someone likes if you’re only familiar with the alternate personality almost everyone adopts during business hours. You might be tempted to find out more about the person they really are beneath that facade, but that requires too much effort and could also come off as kind of creepy. Your best bet is to find something that says, “I was observant enough to notice a thing on your desk I assume you like so here’s something related to that thing I assume you will also like.”

I think most people who find themselves roped into one of these exchanges would love nothing more than the gift of never having to do them again, but sadly, getting companies to stop forcing these glorified team-building exercises down the throats of their employees would take a Christmas miracle.


Don’t. Just don’t. There’s nothing wrong with a group of buddies swapping gifts, but buying something different for all of your friends should be reserved for groups of high school girls who shower each other with presents at the lunch table the day before Christmas break even though they all secretly hate each other but refuse to admit it.

I should stress I’m not being sarcastic or trying to rile people up with a contrarian Hot Take here. It’s one thing to get your buddy a case of beer or a bottle of something for his birthday, but going out of your way to pick up a holiday present is just odd.

I’m sure there are people out there who would defend this practice by saying something like, “We’ve been friends since we were in second grade and have gotten each other something for the past 17 years. It’s our tradition.” Well, stop it. Stop that tradition. Just because you do something for a long time doesn’t mean it’s good. The Big Bang Theory was on television for 12 seasons. That’s all the evidence you need.

If your friend gives you something for Christmas, they’re not really your friend. True friends don’t need an excuse to give gifts. They spend the entire year confusing their buddies by randomly buying them weird shit they found on Amazon without revealing who sent it to them. That, my friends, is what real friendship looks like.

Significant Others

My parents and I wish I had much more experience in this category—especially at the age of 26—but alas, I  do not. Lingerie? Is that what people get for their significant other? I don’t know.

Based on what I’ve heard my girlfriend-having friends say about the topic, it seems like one of the big variables here is how far you are into the relationship. In your first or second year, it seems like there needs to be a lot of thought, care, and money put into this decision. You can’t go too far into “You’re My Soulmate” territory quite yet, but it needs to mean something. This is where the typical girlfriend items should be bought—things like jewelry, perfume, bags; anything that is an actual “gift” and not necessarily something they would go out and buy on their own because they need it.

If you’ve been dating longer than that, then that’s when you start buying everyday items that you know they need but haven’t gotten around to yet, like shoes, jackets, or workout clothes. However, you also need to tread very lightly when you enter this realm and think about potential ways your present could be misinterpreted, as a pair of yoga pants could be viewed as a passive aggressive way to tell her to hit the gym even though you actually bought them because you remembered she mentioned they’re comfortable. It might’ve worked out well for the guy in that Peloton commercial but he was really walking the line with that purchase.

The one perk of getting far enough into a relationship to start getting pelted with hints about marriage is that you won’t have to do a ton of thinking to come up with a gift that year. It’s not without its pitfalls, though, as the biggest downside of proposing (regardless of if you do it on Christmas) is that no gift will ever come close to topping an engagement ring. As a result, you just have to do what you can to show you tried from that point on. It’s hard to go wrong with something sentimental, but based on the commercials I’ve seen, you’ll also be a hero if you buy something shiny at a mall-based jewelry store chain or get a new car for her and yourself without consulting her first, which will always end well.


Buying presents for your grandparents is always weird. They never really want anything because they’ve had at least 70 years to get their hands on essentially anything they could ever want and tend to be terrified of any technology they don’t understand. For example, my uncle got my octogenarian Grandpa a FitBit last year and he hasn’t used it once, primarily because he’s been confined to a wheelchair for a decade. He hasn’t lost his hearing yet, but I assume that same uncle will decide to get him some headphones for Christmas if that ever ends up happening.

As I alluded to before, the only thing grandparents really want is to have some quality time with their family and spend the day slipping every single person there a $20 bill, which they’ll call “our little secret” to make you feel special even though they told all of your other relatives the exact same thing.

They might be difficult to shop for, but over the years, I’ve realized that grandparents are some of the only people on the planet that buy into the notion that it’s “The thought that counts.” Sometimes, you can outsource the bulk of the effort while still getting all of the credit, which is what my family did when we hired someone to write a short biography of my other grandfather’s life before he passed. I had no idea this was a thing, but there was a guy in our area who interviews elderly people for a few hours before turning it into a book, which is not only a cool idea but a win-win for the parties on both sides of the gift exchange.


This is far and away the toughest category of all of these—assuming you get along with your parents and are appreciative of what they’ve done for you. This is not the case with my roommate, who thought I was joking when I asked when he was getting his dad this year before realizing I was serious and saying, “Um, nothing?”

However, if you are in possession of a heart, you look at every Christmas, birthday, anniversary, and holidays that only exist because of greeting card companies as a way to give props where props are due. You’re kind of obligated to think outside of the box there, and even then, there’s a chance you’ll still be worried you didn’t make the right call even after they react with seemingly genuine joy after when open it. I know I took a big dump on the warm and fuzzy feelings that come with giving gifts at the start of this, but when you spend years disappointing your parents, it’s nice to be able to know you were able to make up for it a bit by nailing your present.

If you have siblings, the best move is to make these a team effort. My brothers and I usually all pitch in (which, as the oldest, means I pay for it and spend weeks reminding them to confirm my Venmo request), which means you can impress them with some bigger ticket items compared to what you’d be able to swing on your own. I keep telling myself I’ll eventually have the means to pull a Pavin Smith and pay off their mortgage, but for now, I hope dad is happy with some Bruce Springsteen memorabilia and mom will be able to get some mileage out of her new winter coat.

It also doesn’t hurt to throw in a solo gift for good measure (if you’re really trying to maximize your return in their will, make sure to tell your siblings you aren’t planning on doing this). When you consider you’ve already blown them away with that cool new kitchen appliance, this is just a bonus, so you don’t have to break the bank to find something they’ll appreciate. You want something that’s small but practical so that when, say, your dad goes to fix a divot or your mom throws on an apron in the kitchen, they’ll be subconsciously reminded that you love them more than any of their other children.


It’s easy to half-ass this one because you don’t want to make your siblings think you care too much about them but you also have to think about things in the long term. If it’s obvious you didn’t put in any effort, you’re not only probably going to get pulled into the kitchen by your mom for a lecture but are also tempting retribution if whoever you shortchanged gets you a similarly shitty gift the following year. Above all, this is an investment; it might take some time to see results but the returns should justify the wait you have enough patience.

The gift itself is kind of an afterthought. It doesn’t really matter if it’s something they’ll use as long as it’s related to something they like (which is mostly so your parents think you took the time to carefully consider your options) and doesn’t cost less than $20. With that said, if you go with a higher pricepoint, your siblings will likely feel the need to reciprocate the next time Christmas rolls around. If you play your cards right, this gift-wrapped arms race will continue to escalate over time and you’ll be able to emerge as the victor when everything is said and done.

Now, I know that doesn’t cover all of the bases, but it should at least make Christmas a bit more manageable. In the end, gift-giving is a tough task regardless of who you’re giving them to, but I think it’s worth the hassle. It’s nice to be able to walk around telling yourself you’re a good person and convinced that you’ll be rewarded with some good karma for all of your acts of goodwill—ideally in the form of a pile of gifts that justify all the work you put in leading up to December 25th.

In all seriousness, this is a busy and stressful time of year, but getting to take a break from work, spend some time with the people you love, and seeing everything come together in the end is what makes this the best month the calendar has to offer. That magical feeling may just be a distant memory by the time you audibly gasp when you look at your credit card statement after the dust settles, but when you do the math and realized you came out the other side $27 richer, you’ll be reminded why you put up with everything each year.