The Stable Marriage Problem 🐘
Ajeya Cotra goes into the “Stable Marriage Problem” algorithm to explain why Asking for what you want opens up you to opportunities that may be outside your usual band of possibilities.
… I think the core dynamic in the proof of asker-optimality and askee-pessimality does apply to real life. If you only ever pick from offers you get, you never try anything unless someone out there already knew you and liked you enough that they took the trouble of coming to you. If you ask for stuff, you get to pick from among the entire universe of potential options theoretically available to you — and who knows, it might work out.
In my own personal experience, I can count many, many things I have gotten by asking, even (especially) things in retrospect, I had no business of having. However, it is always good to remind ourself that it is a muscle that atrophies if you don’t exercise frequently. So, go ahead, and ask away!