If course I was never scared to ask someone out of the blue if they wanted to go on a date. I always figured if they said no, I was one step closer to one that says yes.
My wife uses that exact philosophy in her business.
Cheese.....
And don't forget, "No" means just that, "no". It is not a statement of your attractiveness, personality, dress, breath, body odor, or anything else. Unless they tell you "No, you're a nasty little troll and I'd rather date Jamisjockey..."....."No" is not a rejection of you, its just a rejection of a date.
Rethink how you phrase the question. There is a pinciple in sales....the hard sell.
"Do you want to go on a date?" Leaves them with a yes or no choice.
Instead, use the presumptive sales approach:
"We should go get coffee, or maybe dinner....which sounds good to you?"