There are programs and books on this subject. I'm not an expert, and I need this education also; so here's a quick starting point I just found: https://daringt

There are programs and books on this subject. I'm not an expert, and I need this education also; so here's a quick starting point I just found: https://daringtolivefully.com/how-to-ask-for-what-you-want https://daringtolivefully.com/how-to-ask-for-what-you-want This may not be the best starting point, but it's a place. A friend took some coaching class once where they were given "scary" human interaction challenges, starting with very small simple ones and working up to ones where you would expect to get slapped. Not only did it help condition my friend to be more outgoing, but he got a surprising number of "Ok"s. I'm not sure this is the best approach, but it appeared to be effective. And it reminds me of this guy: https://www.youtube.com/watch?v=-vZXgApsPCQ https://www.youtube.com/watch?v=-vZXgApsPCQ