If you have to hit on/flirt with/make eyes at a woman, make sure a) she’s available, b) she wants you to flirt with her, and c) she is well within your league. The first two should be stupidly obvious. I don’t feel I need to elaborate.
However, when it comes to c, there’s something you may not know. …Now, get ready. I’m about to reveal an uncomfortable truth. Hope you’re sitting down.
When an unattractive man (let’s say a 2) hits on an attractive woman (9), she gets upset. She’s not upset because a guy hit on her. She’s mad because a 2 hit on her. (Are you with me so far?) Clearly, a 2 shouldn’t bother hitting on a 7, let alone a 9. (What would be the point? That’s far out of his league!) In this example, in her mind, the best case scenario is that this 2 has a stretch goal of bagging a 5. And if the 2 thinks the 9 is a 5, he has just dealt a huge blow to her self-esteem.
League math. It’s a real thing.
This is also one of the reasons why the overwhelming majority (87%, according to a survey I just made up) of sexual harassment cases are brought against ugly dudes. Of course, more attractive men probably don’t have to try as hard as their less attractive counterparts… But really, ugly dudes thinking they have a shot with attractive women? It’s insulting, counterintuitive antiscience.