The Great Filter

I get the introductory conversation.

I get the good first impression.

I get the phone number.

I get the text conversation.

But

I do NOT get the hanging out/date. This is The Great Filter.

I have the mental plan all laid out, but the ball never gets rolling. A strange mix of emotions (fear, but some other harder to describe one) gets into play which I allow to stop me from ever making plans. That or I make plans but for whatever reason, they can’t do it that day, and I never ask again, forever waiting for the ball to be thrown back to me.

My question is:

How do I get past The Great Filter?