some of it is that i ask regardless of how afraid i am. at least with existing friends and loved ones, i ask a lot and the more i ask and the more they say yes, the easier it gets to. as far as forming new relationships of any kind, i try to go in with very few expectations, i'll usually just say hi and that i think the person is cool. If that leads to a longer conversation about literally anything it's easier for me to keep wanting to talk to them, and what i said before holds true, the more i talk with someone the more i trust them and the easier it is to not be afraid i'm bothering them