Bruh 100 times is really creepy. Try once, and if that fails, try one more time after you give it enough time. After that point just give up my guy.
(I would say try once and move on, but I've heard from multiple women that they'll reject someone the first time even if they're into them just because they want the person to "chase" them or w/e. Which is juvenile and dumb as fuck and honestly you're probably better off not being with someone who plays those kinds of games, but if you're really into them stop at 2 tries.)