Ask and get rejected. Ask and get rejected. Ask again and get rejected again. Get rejected so many times the sting wears off. So many times the rejecters no longer look like viable prospects but merely part of that large crowd of people you don’t really want to have anything to do with anyway.
Keep asking until one day he says yes, no better than that, he says, “Would love to! Expect a call soon!” with a smiley face and everything. Then go out on a date. A great, great date. Not because of what you did, because of who you were with.