Not a shadchan, but will answer anyway.
1- There are lots of dating books. I pretty much read all of them by the time I was 14. They are pretty useless unless you really need a book to tell you to have some self respect and get dressed up for dates.
2- Ask a Rebbetzin.
3 – At least you realize it’s hypocritical. I think the best thing is to try to figure out what each person needs, and which other person can help fill those needs while also getting their needs. Sorry I’m muddled tonight but I hope you get what I’m trying to say.
4) No idea, sorry.