This is pretty common advice:

Ask for what you want. What’s the worst that can happen? All the person can do is say no.

This is a bizarrely short-term way of thinking that is pretty pervasive.

Of course, the worst thing isn’t just that they say no, it’s that you erode your social capital! The reverse situation makes it obvious: haven’t you been asked for something, the request is tiring, and you cut ties with that person?

I have to do that constantly, and did it just now (the cause for this post).

This doesn’t apply to things that require asks, like salary negotiation. This applies things like asking for favors.

Give so much to others that you know deep in your heart that they’re indebted to you. You won’t feel any worry about the ask because you know it’s a valid request.

If your stomach is churning before you make a request, examine it. Have you given more than you’ve received, or are you being annoying?