Hello, as the title says, this guy I know from high school, is becoming very lonely because literally every single girl turns down his advances. I'm not close friends with him but he is always trying to maintain a conversation with my sister, and she sends me screenshots frequently because the level of desperation is beyond anything you could imagine. My sister and I both feel bad for the guy and he needs serious help. I want to find a book to suggest to him but I am having a hard time finding something so hopefully someone here has some ideas.

Overall he is a good person, and his social skills in person aren't bad at all. But he is always messaging girls over social media, and just saying the most pathetic cringe worthy shit, its so bad that he cant even get a 0/10 girl, I am not kidding. He is always fishing for compliments over facebook, posting the most pathetic shit like a picture with a caption like "my last post hardly got any likes, could a few girls please like this to make up for it", and then any girl that likes it he immediately messages and tells them how lonely he is and how badly he wants a girlfriend.

So, does anyone know of any good books this poor man should read? Brutal honesty for this guy is okay and probably encouraged.

Thanks!