Ruby's Ultimate Guide to Thoughtful Gifts
the most comprehensive guide you ever did read
Give a man a gift and he smiles for a day. Teach a man to gift and he’ll cause smiles for the rest of his life.
Gift giving is an exercise in theory of mind, empathy, noticing, and creativity.
“What I discovered is that my girlfiend wants me to give her gifts the way you give gifts.” – words from a friend
How hard your gifts hit the joy receptors depends on how good you are at giving gifts. Time and money alone are not enough to produce gifts that reliably delight; skill is required. Skill is what I am here to teach. My purpose here isn’t to lift specific suggestions, but through theory and examples to teach you how to think such that you naturally give good gifts
This is a long post but it should permit jumping around and just reading what catches your eye. It’d make me happy if you still read each of the three theory sections.
Table of Contents
Caveat: gifts don’t have to be objects
I’m going to talk a lot about objects, but some of the best gifts are cards, letters, shared experiences, and so on. Hold tight, those will be covered too.
What do you know about them?
In the modern age of abundant hyper-specific goods, advanced manufacturing1, and global shipping, there are dozens of trinkets to go with any hobby or fandom.
Gardening, paragliding, Warhammer 40k, crocheting, nail polish, rock climbing, hiking, vampire novels, parenting, collecting coins, crocheting, baking, collecting succulents, Sabrina Carpenter fans, and so on. For any of these interests, there will exist great gifts across budgets.
Once upon a time, it might have been the case that if someone was into a hobby, then they’d have all the basic tools and if you went into the local store, it’d be hard to find something they didn’t already have. These days, there are so many things that there’s no way anyone has all of them.
Plus, there’s abundant information to find out about their existence. I don’t know much about gardening, but just as I’m writing this, I searched “great gifts for people into gardening”.
Etsy often has cool stuff so I clicked in. Lots of cute, pretty things I might go for if I’m going for an art or decoration-type gift. Going breadth-first, I come back to the search results and click into a Reddit thread. Such threads are great because they’re actual people sharing what they liked and why, rather than paid reviewers.
Hori hori knife seems promising. Amazon has a whole page of them. Amazon also has a whole page of unique gifts for Gardening folk.
In 10-15 minutes, you can pick out a specific, thoughtful gift that is meaningfully helpful or brings delight. And not necessarily spend very much! A well-chosen $20 tool can have more value than a $75 random thing of no use. If I were choosing something pretty rather than practical, I might have gone with this cute teacup bird-feeder from Etsy:
I picked gardening as an example because it was the first random hobby I chose for my list above. I bet this process works for any of the others.
“Life transitions” can be as helpful as “interests”
Someone setting up a new apartment from scratch is a great opportunity for gift giving. Consider a nice spice set. Consider the household items you most value.
Another major life transition is having a kid. If you’re a parent, then you likely have opinions about the great things to own. Even if you’re not, it’s not hard to research.
What if you don’t know them?
It’s my cousin Mirna, you say, I was assigned to get her a gift and I don’t know her at all!! Poppycock. She’s human and you’re human; in other words, you have a lot in common and there are dozens of great things you could get for any human.
Not everyone knows that there are now bug bite itch relief tools that work pretty well, like this one or this whole Amazon page. As above, modern industrial society has delivered. I searched “cool useful gifts” and another sweet Reddit page, Cool gift ideas - things people didn’t know they wanted. Jackpot.
Simple but meaningful
Here’s a different angle for your gift giving. Go to your person’s Instagram or Facebook, find that badass photo of them paragliding. Save it. Search “AI image editing”. Search “AI image upscale”. Take that image, make it look good (lighting, colors, etc.), then search “custom printing” and find an option like canvaspop.com and print that awesome image on some cool format. People out in beautiful nature shots go well on canvas prints. I’d guess cool action shows would fit thematically with metal prints.
(If you have the budget, buying someone a photoshoot is a great gift.)
Or make a whole photobook. Make a photobook of their pet – if someone really loves their pet, they’ll really love a photobook of them.
Another way to add charm here is to find a neat frame for whatever it is. Framing is nice but it’s extra effort and “optional”, so people often won’t do for themselves. An idea: I’ve seen thrift stores have crappy old framed art. Buy it, throw out the art, and put in your new thing with a neat vintage frame.
If you’re stuck on how to do any of these steps, ask an AI. They’re great assistants for finding websites for these kinds of things.
If you can delight yourself, you can delight others
The skill of improving your own life extends to improving the lives of others.
First, things that were valuable to you are often valuable to others. There are various objects I find to be great that not everyone has; these make for great gifts. For example, a portable jump-start battery for cars. Vastly more convenient than jumper cables.
Or to step away from problems, if you’re good at finding things that bring you joy and satisfaction, you can help others find it too. This might look like noticing that a particular brand of tea, prepared in a particular way, is amazing.
That itself could be a good gift, but the skill of noticing for yourself helps notice for others: both for problems to solve or opportunities for joy.
If a friend knits, I could walk by the textile store and notice some particularly nice and interesting yarns for sale. The key thing is to have your mind keep noticing opportunities.
You want to be the kind of person who, even though you don’t experience sinus pain yourself, upon seeing an ad for a sinus pain relief device, remembers that your partner or friend suffers from it.
Theory 1: Something they want but don’t yet have
Time for some theory!
A great gift is something a person wishes they had but doesn’t yet have for some reason. Your mission is to overcome those reasons.
Broadly, a person fails to have something they want because either they don’t know they want it (very common!) or, despite knowing they want it, they lack the ability to gain it for themselves. Often both!
My opening advice was focused on the didn’t know case. You are gifting them some number of dollars, but also the minutes of time you spent searching (or your pre-existing knowledge). Let’s talk about couldn’t get it on their own case. There are multiple possible reasons.
In my case, there are a lot of things I don’t have because research and shopping take time, even though I would spend money on an item or experience. An easy way to win right there.
Obviously, money is often a factor. This is what makes it so easy to delight kids: they’re poor and it’s not weird to transfer large amounts of raw value to them. Be the popular uncle and buy that PS5. With adult-to-adult gift giving, it’s a little more fraught to spend a lot2. Gift-giving often involves reciprocity expectations and, as a result, unwelcome indebtedness if a gift is too large. The thing is, there are so many ways to make for a great gift that aren’t spending more on it. Hence this post.
Then there is a whole class of gift where, despite wanting it, a person could not obtain it for themselves even with time and money. Skills, opportunity, and sentimental value are chief culprits.
Skills: my dad builds me a custom birdhouse for my yard when I myself lack wordworking skills.
Opportunity: my friend knows EJAE personally and gets me her autograph with a personalized “dear Ruby” message.
Sentimentality: I bought a vase for my mother. I wrote a love letter to my spouse. I picked out flowers and remembered which were my friend’s favorite. People can’t gift themselves things from you. Where the from you is a key part of the gift3.
We can conveniently lump these as SOS (Skills, Opportunity, Sentimentality).
Into this last bucket I lump the range of (i) it is you who is giving the gift, and (ii) in giving the gift, you reveal that you remember/see/understand/care.
Skills and sentimental value are a particularly potent combination, as I will show in my upcoming examples.
Travel is great for gifts
Ten plus years ago, a friend of mine worked for the Red Cross in Bhutan. She brought me back a locally-made scarf. It’s sentimental because she gave it to me and it’s special/unique because I don’t think I have an easy affordance to get items from Bhutan.
Travel gifts don’t have to come from the other side of the world. Take a day trip to near where you live, stop in a small town and peruse the thrift store and they might have some neat items that make you think of someone you care about. You can gift it and say, “I was passing through Fortuna and stopped at this little store; this glass bird made me think of you.”
In a world of Amazon, there’s a romance to that. Items with a story that come from an origin more personal than the online, add to the sentimentality.
What are your skills? Play to your strengths
Skills are extremely powerful when it comes to gift giving. At their most boring, they can allow you to gift some with a large amount of raw value at low cost to you4; at their most interesting, they allow you to deliver unparalleled gifts that score high on skill, opportunity, and sentimentality.
Of all the gifts I have received, I think the one that touched me most was a recording a former partner made for me. She recorded herself singing a cover of a love song for me, including playing accompanying piano herself too. I have no musical training myself, and it was just so touching.
If you are musical, record someone a song. If you have visual art skill, draw them a picture. If you know how to construct anything, make them something5. If you have medical training, pack them their own personalized first aid kit. If you code, make someone a little app or website. If you’ve got a green thumb, pick out a neat plant and a pot and gift it to them with instructions on how to care for it. If you write stories, write a little short story where the main character is inspired by the recipient.
What if you don’t have any skills? What? Why don’t you have any skills? Go get some skills, bro.
But actually I don’t believe you. Everyone has skills of one kind or another and with a bit of creativity, many skills can be turned to gift giving. Momentarily, I'll share how I used my data analytics for one of the best gifts ever.
At a basic, you speak some language and know how to write. Words are powerful. Also, it’s the fucking thought that counts. You don’t even have to be that good at music, art, or writing for a genuine effort to be touching.
Write a goddamn letter (the power of words)
Words are powerful. Words can stay with people and go deep. If you have someone who matters to you, one of the best things you can do for them is put that into words and write it down.
It doesn’t have to win a Pulitzer; your recipient will only be judging you against their estimate of what you could do if you were trying. If you’re not that wordy of a person, it’s all the more touching.
Plus the embellishments!! Buy nice paper, a nice pen, and write your letter out by hand. Fucking charming. Pro-tip: you can still draft on a computer where editing is easy, and then transcribe it to paper. Get some nice envelopes. I have a stack of red ones I use for love letters.
Write a poem! Doesn’t have to be good.
But for goodness' sake, don’t use an AI chatbot for help in writing. You will muddy all authenticity if you do so. Either clunky AI style will come through, or, when the chatbots invariably improve, it will be suspiciously good. I suppose at some point, they’ll be so good they can produce what you would have produced if you tried your hardest. But it’s lame. Put in the real effort and be authentic. Be able to honestly say “I wrote this myself unaided6”.
Cards are wonderful
Cards are an opportunity for thought and creativity. I have found that even the local drug store has enough variety that I can pick something tailored and meaningful to the relationship and occasion. Book stores often have a greeting card collection that’s a little more artsy and varied. Nor am I against hunting online.
A Note on AI Tools
Above, I said For heaven’s sake, don’t use AI to help you write. I don’t share that sentiment for AI visual art and AI music. At this time, getting good results from them still requires human skill. Moreover, making good art for someone will build on your understanding of them and their likes.
For example, I recently made my spouse howl with laughter by using AI to quickly make an AI song ~parody of her fictional world and characters.
And as above, I endorse the use of AI as a search engine or for practical help, like how do I build a birdhouse that looks like <photo>. Though the most meaningful gifts will require you to come up with more bespoke lines of query than “cool gifts”. (Though that’s fine for casual) gifts.)
Theory 2: To be seen and to be cared for
Every gift sends a message, and it’s a good question to ask which message an intended gift will send. One of the best messages is “I see you, and I care about you.”
Naturally, people want to be cared for! And as part of that, they want to be seen, noticed, and understood for who they are and what their specific wants and needs are. This underlies the value of customized gifts. What gives thoughtful gifts their power is that they demonstrate both the noticing a person and the taking an effort to use that knowledge for their benefit.
A little goes a long way. Just paying attention to someone’s interests and doing something appropriate (as in the opening sections) does this. For some more examples, here’s what I’ve gifted family members in years gone by:
Father, into cooking: a high-quality Japanese knife
Mother, into reading: Kindle Fire tablet
Grandfather, into planes and aviation: toy drone
In-laws: also the kitchen knife
Brothers: mechanical keyboards (see below on self optimization, other optimization)
Sister-in-law: high-quality headphones
Brother-in-law, into music: a stylophone
For my birthday this year, my parents gave me a little model car. I wouldn’t give them that many points for knowing my interest in motorsport, but this gift revealed more attention and effort: they’d picked my car, an MX-5 Miata and found it in the same color as my car.
Flattery usually goes well. I don’t actually wear them, but I liked receiving the “Best Dad Ever” socks. I once gifted my nurse spouse the following:
Ultra-Powerful Gifts (stack your gift elements)
The very best gifts I have given combined my skills, creativity, knowledge of the recipient, and our relationship. If you crank the dials up, you can produce really touching gifts.
You might think that only some skills lend themselves to gift giving. I say more skills than you think. I have a Data Science background and know how to work a vector graphics software. This can be turned to a gift.
For our fourth wedding anniversary, I downloaded all the chat logs between me and my spouse. I analyzed the logs, produced this academic poster with the results, and had it nicely mounted on foam core board. Apparently, it’s still the best gift I’ve given7.
You ought to know a few things about my spouse: she writes a lot of fiction, she likes snakes and has her own pet snake, and in 2020, she had her right leg amputated due to osteosarcoma.
For one birthday, I teamed up with a friend who runs murder mystery parties and is also a huge fan of my spouse’s writing. Together, we wrote a whole murder mystery set in my spouse’s fictional world and invited a crowd to join. My spouse got home, I blindfolded her, threw her in an Uber, drove to my friend’s house, put a costume on her, un-blindfolded her, and the party began.
I used to co-write little fictional scenes with another partner. One time I thought up a long list of scenarios. Yet! My job has prepared me for making book covers8. I formatted the list nicely with careful font selection and mocked up a book cover that wouldn’t have been out of place in the fantasy section of a bookstore. (No image for privacy reasons.)
The gift I am perhaps pleased with is the statue. I don’t remember how the idea came to me. But my spouse is beautiful, likes snakes, and is missing most of a leg. During Covid year, I made this the pictured statue. Start with an Eve bronze statue, use a hacksaw to remove the leg, and some files to smooth it down to the appropriate shape.
I don’t remember at all where the idea for this came from, but the way my gifts usually go is I start with one idea and then keep thinking of further improvements. In this case, I might have had the idea “woman with a snake”, and then once I was looking at options, realized I should shape it to match my spouse.
In short, the best ideas aren’t always 0 to 100 instantly. Start with one thing and build on it.
A different great gift is how my spouse took our wedding vows, and for each phrase she generated an AI art image and overlaid the phrases onto the image, “quilted” them together, and made a poster that now hangs on our wall.
To link back to the theory we’ve been covering, the above gifts:
Require skills that not everyone possesses, so the recipient might not have been able to produce them their selves
Have a lot of sentimental value: they concern the specific relationship and it’s meaningful that the giver gave them
Send a message of I am paying attention to you and us, the details matter.
Are creative. Creativity is a skill, but it is important enough to list on its own.
Meaning doesn’t have to be grand!
Most of the gifts I have ever given were not as bold as the above. I wanted to show what it looks like to turn the dials up, but you don’t always have to in order to delight.
Hanging in our house is this poster that my spouse ordered for our second anniversary. It has the position of the stars on our wedding day plus the phrase we most often say in response to “I love you”.
This poster is made by a company when you give them dates, location, and a phrase. The impact of this doesn’t come from investment into the gift, it comes from the investment into the relationship. The gift is a token for the relationship. We got married. It’s a reminder of that, and that special day, and our relationship, that I see hanging on the wall all the time.
I like the companies with services like this, that help produce meaningful artefacts. There’s another similar one I saw recently – you give them a location and they make jewellery using the street layout surrounding it.
Experiences are fundamental
We don’t enjoy objects, we enjoy experiences of objects. Experiences are more fundamental.
Relationships aren’t built out of exchanging objects, they’re built out of sharing experiences.
Among the best gifts are those that cause experiences for the recipient, or even better, for the recipient together with you.
But tickets for shows and classes. Buy giftcards for tours, boat cruises, and museums. Buy memberships for the botanical gardens, the Academy of Sciences, and so on.
The father of any early girlfriend of mine bought her two tickets to a 3-hour-long barista training course that I was lucky enough to join. She really liked coffee (this was back in Melbourne). It was a really interesting experience I remember fourteen years later.
Think about what your person likes to do or might like to do but they don’t know. Asking what experiences would be good is also a good guide to gifts. Perhaps they like cycling, in which case new cycling gloves or an emergency puncture kit could help facilitate that experience.
Don’t know which experiences could be good? Search engine. Or glorified search engine, aka AI. Ask what’s good to do in your city. Also note that AirBnB branched out hardcore into “experiences” alongside lodging.
Coupons: the magical way to turn experiences into objects
Typical gift giving involves the transfer of some item. Gifting has the nice tradition of physically handing over an item to someone, and then they get to unwrap and/or open it. On Christmas, people pile up the gifts under the tree.
I’m in favor, but it makes gifting experiences awkward. It’s just not the same to say to someone that you will take them out to a fancy dinner. Fortunately, some ancient gift innovators whose names are lost to us pioneered the use of coupons – you simply write down the experience you are gifting and give your recipient that paper: the intangible becomes tangible.
If you want to know how powerful coupons are, consider how they are favored by children. Owing to their limited skills and resources, it can be hard for a child to give a thoughtful gift, yet coupons empower them to gift the non-physical things in their power. Look at the charming example below of a coupon book made by children.
If you’re unwilling to gift no whining, consider that all the following would make for great coupons: a long phone call when you need it, ten hugs, listening attentively to your latest interest for 20 minutes, going out for ice cream, making your your favorite meal, a really solid back massage, a trip to your favorite restaurant x2, a long stroll in a location of your choosing.
The coupon represents the resources you have earmarked for your person. And the choice of coupons can be used to signal that you see the other person, understand their wants and needs, and would like to fulfil them.
It’s also totally okay if the things you’re putting on the coupons are normal things you would have done anyway. It’s still sweet, it can add security to the relationship, it can inform them of things they didn’t know you were willing or able to do, and it provides a clear affordance to seek someone out, e.g., a long phone call on a day they really need but might have otherwise hesitated.
If aesthetically, coupons don’t have a vibe you like. That’s okay, you can call them promissory notes instead ;) Speaking of aesthetics, coupons combine well with cards and envelopes, and there’s great scope for creative presentation there.
Etsy comes through as usual with many results for custom coupons. You can buy them or just take inspiration. A couple of ideas that occurred to me while writing this: buy a little wooden box, write each coupon on a small piece of paper, roll them up into scrolls, tie them with string, and place them in your little gift chest. If your person would like cute figurines, get some of those that have removable heads or some other cavity to place your coupons into. A little creativity goes a long way. If the chest is going to someone you live with, you could periodically top it up with new coupons/scrolls/coins.
Aesthetics & Symbolism
I love these for gifts, and the two go together as the aesthetic can be shaped to the gift and recipient. Themes are great. If I was doing coupons for my spouse, an ardent medical professional, I might present it as doctor’s prescription scrawled in barely legible handwriting: hugs, taken morning and night as needed,…
If it wasn’t apparent already, I’m a fan of Etsy for items and for inspiration. There’s also Pinterest, though I feel like it has degraded it recent years. You can ask AI chatbots for design inspiration, including asking them to find websites with examples.
By symbolism, I mean don’t just buy someone a piece of jewellery. Gift someone jewellery with a blue stone because it matches the color of their eyes. Gift someone something made of black leather, because to you they are hardcore. Gift someone columbine flowers because those were all around you when you went for that very special picnic one time.
If you’re writing something, think about the font that matches the recipient and the mood of the letter. Serif, sans serif, etc. You can describe the mood, what you’re going for, and an AI chatbot can help you there. In this case, it’s functioning as a tutor – and I think it’s worth learning a bit about typography. Also, learn to pick and match colors well.
Easy Style: Wrapping Paper, Bows, and Ribbons
Acquire for yourself out-of-the-ordinary wrapping paper and ribbon, and learn how to tie that ribbon around a box. (If that’s too hard, there are stick-on bows too.) Boom, extra charm added to your gift.
Start Early
Your pool of options shrinks drastically as the time until the gift is needed shrinks. If you’re not fussy and live in the US, Amazon Prime shipping can you a colored envelope in a couple of days. If you’re going for a particular aesthetic and need a specific shade of green, that might come from a seller with only 2 weeks of shipping. Etsy order deliveries often take weeks. If you’re crafting something yourself, it’s nicer to not feel rushed.
The gift of laughter
Don’t get the wrong idea, not every gift has to be eminently practical or deep and serious. You can have fun with them. If you have a friend a couple of years older than you, buy him hearing aids for his birthday. If you have a lover, give them a lump of coal with a note that says it’s been great being naughty with you.
Get them socks with their face on them or something else ridiculous. Amazon and Etsy both have pages of gag gifts. Give them a card apologizing for sleeping with their brother; when they say they don’t have a brother, ask then who did I sleep with??
Friendship is countersignalling. Give a gift that says, I think we’re such good friends that I can get away with giving you this.
Even better, play on inside jokes or things that only the two of you would get. Marmalade.
Books. Don’t forget about books.
I’d be remiss if I didn’t remind people that books are something you can gift. Despite generally being a fan of online shopping, I’d say go into a physical bookstore where you can easily browse. (Bookstores also often have interesting and aesthetic greeting cards.)
For something special and symbolic, try visiting a second-hand bookstore and picking out something old and exotic like a recipe book from 1946 and a physics textbook from 1962. Something fitting for who the recipient is.
Theory 3: Empathy, noticing, and creativity
It’s easy to be cynical about gift giving. Capitalism has distorted it into a soulless rite where you buy some “on sale” doodad the recipient probably doesn’t want or need in order to discharge a social obligation.
We shouldn’t let gift giving gone wrong make us forget that gift giving can be great.
Good gift giving trains habits for strong relationships. Gift giving is one of the five love languages for a reason. First, realize that the act of giving great gifts isn’t something that you do just before Christmas or just before their birthday. To give great gifts, you need to be paying attention to the recipient to one degree or another. Listening to them, remembering them, taking an interest in their interests, and imagining what it’s like to be them (likes/wants/needs/challenges).
Combine that with creativity: thinking outside the box, not just taking items off the shelf but carefully combining chosen pieces and elements so your gift is thoughtful both in substance and presentation. A good gift is art, and I reckon it’s healthy for humans to be artists.
By doing those, you unlock the ability to create phenomenal gifts that signal the love and care that you hopefully feel for at least a few people in your life.
Happy gift giving!
Well, I’m afraid I’ve run out of puff. I think this blog post is a good start. It’s not perfect, but that’s the thing – gifts don’t have to be perfect either. People are so busy, so rushed, so cynical that taking just some time and some effort means a lot. So good luck to you, mighty gift-giver, bestower of beauty and joy. Go forth and bring joy!
If this post helps you give a better gift, I’d love to hear about it in the comments. <3
For example, widespread quality affordable 3D printers mean that people are making small runs of interesting doodads for their hobbies all over the place.
Though if you’re the well-to-do cousins in a family where others struggle, a generous gift card might be the most thoughtful and valuable thing, and I won’t tell you otherwise.
From you works well for gifts to your mother, less well for contributions to the office white elephant exchange. In the latter case, the gift has to carry its own weight – but that’s easy.
For reasons that don’t matter, it’s more okay in our culture to gift “services” to others worth a lot even if it’s fraught to gift valuable objects.
Crafters have long known that you can knit someone a sweater or sculpt them a mug. To them, I merely caution that you need to keep it fresh. A mug every year will not be special. So either find some variations or reduce frequency, or both.
I think it is probably okay to use the chatbots to check for spelling and grammar issues, and perhaps some help with finding good synonyms, but it is risky.
Which is saying something, because I gave that woman a child.
I did not actually design any of the LessWrong book covers, but ambient exposure to the process and related typography and image-generation work meant it was no stretch.
This is an excellent post. I already use a few of these ideas so it’s great to get a few more.