Mostly it depend on our own insecurity, and the fear to be rejected, many have it, including me in my youth...well maybe still
If we manage to build our own self-confidence, such thing will become much easier, and the pain, if rejected, might be lessen...so that must be a goal for most of us
I have found meditation to give good benefits, to realize that the world will not collapse if we are defeated now and then, to understand that if we want something, then we must also try to reach for it, the more we do so, the easier it become...but it takes determination to start.