Incels. Incels and gullible teenagers who later become incels.

Perhaps someone who is trying to form a connection after spending their youth not completely understanding social conventions....

It just feels kind of mean to dunk on him this hard for something so minor. He's not reading Jordan Peterson or anything. It's obviously someone trying to better themselves...they're just doing it in a way that makes us cringe.

Like it's fine to laugh at the situation but have some empathy, too. They weren't acting maliciously

Zapp Brannigan's Big Book of War is a classic though.

Only a very stable military genius uses the strategy of exhausting the enemy's ammunition until they run out on your own troops.

I would not be surprised to learn this person has autism and takes the world in a very literal manner, so even though they need coaching to develop social abilities, reading a book like this is not particularly helpful.

Someone who doesn't interact well with people romantically or otherwise. I feel like flirting is 80-90% just being friendly and personable with maybe 10-20% flirting, especially early on. If they don't understand how to to do the 80-90% well, they're going to be grasping at straws figuring out how to relate to someone.