You shouldn't have to work up courage to ask out a girl, if your heart is in the right place the courage will come from God. You shouldn't go around asking girls out all of the time, almost like a salesman approach to dating, it's thoughtless. I think dating is for people who settle for a bad story. You shouldnt just try people on for size, in any capacity. I believe in Jesus for the fulfillment of deep desires, and He never does anything shabilly. He always exceeds expectations. So dont try to make it happen yourself. It simply will not work......Just do what you know God is telling you to do and His blessings will over take you. At 26 I have seen many cheap stories and only a few extrordinary ones...i think the trick is a pure heart and being patient. When You really love Jesus more than Life itself...the needs fade away in His Glory anyways. Focus on Him, He's where it's at anyways!!