One of the expressions I hear a lot in the startup world (and which I even use from time to time) is "it's a numbers game."
What the speaker means is that in certain activities, such as selling a product, pitching a VC, or asking a woman out, failure is the most likely result, and that the only way to successfully achieve the desired outcome is to be persistent and make multiple attempts in the face of rejection.
This is good advice, but it's critical that we treat the "numbers game" as a heuristic, not a physical law.
In general, persistence improves your chances of success. But that doesn't excuse you from using your good sense.
For example, heterosexual men have to learn to deal with rejection; the majority of the time that a man asks a woman out, she's going to turn him down. Or at least, that was my experience when I was young and single!
A man who gives up on dating after a single rejection is likely to remain a lonely Hacker News reader (I kid! I kid!). You have to keep risking rejection if you want to find a woman who is actually interested.
On the other hand, a broke, ugly, unknown man who insists on asking out wealthy supermodels will never get what he wants, regardless of how many of them he approaches (and gets slapped by). Even the supposedly ugly men who have landed supermodel wives (Billy Joel and Ric Ocasek come to mind for me, which shows you that I've reached geezerhood) are rich and famous, which is apparently more than enough to offset being ugly.
If you want to figure out if the "numbers game" principle applies, just use math. If you have a one in 10 chance of success, and you make six attempts, you have a better than 50/50 chance of being successful at least once. If you have a 1 in a million chance of success, your chances after six attempts are better, but are still just 6 in a million.