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“Ruby’s Ultimate Guide to Thoughtful Gifts” by Ruby


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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

  • What do you know about them?
  • What if you don’t know them?
  • Simple but meaningful
  • If you can delight yourself, you can delight others
  • Theory 1: Something they want but don’t yet have
  • Travel [...]

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Outline:

(01:06) Caveat: gifts don't have to be objects

(01:22) What do you know about them?

(04:05) What if you don't know them?

(04:45) Simple but meaningful

(06:05) If you can delight yourself, you can delight others

(07:27) Theory 1: Something they want but don't yet have

(10:18) Travel is great for gifts

(11:25) What are your skills? Play to your strengths

(13:16) Write a goddamn letter (the power of words)

(14:38) Cards are wonderful

(15:01) A Note on AI Tools

(15:49) Theory 2: To be seen and to be cared for

(17:55) Ultra-Powerful Gifts (stack your gift elements)

(21:55) Meaning doesn't have to be grand!

(23:01) Experiences are fundamental

(24:37) Coupons: the magical way to turn experiences into objects

(27:55) Aesthetics & Symbolism

(29:36) Start Early

(30:05) The gift of laughter

(30:56) Books. Don't forget about books.

(31:32) Theory 3: Empathy, noticing, and creativity

(32:50) Happy gift giving!

The original text contained 8 footnotes which were omitted from this narration.

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First published:

November 28th, 2025

Source:

https://www.lesswrong.com/posts/dmLnWjyqAi5N2pqqz/ruby-s-ultimate-guide-to-thoughtful-gifts

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Narrated by TYPE III AUDIO.

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