Reply To: which is more painful?

I think #1 is worse, because you have been rejected for NO reason; the person did not even meet you to make an informed decision. After one date it might feel worse to have the other party say no to a second date, but it really is not, because at least that decision is based on having met you and not feeling this would be shayach to go further. But to say no out of hand, without ever meeting you in person – that would make me feel awful, because you are not even getting a chance to make a good impression.