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I'd recommend no more mr nice guy if you are a pushover

Yes experience is better than reading but the psychologist James glover snapped on that one

Sounds crazy but working out is the best thing I find for this not any by the book tactics.

Not saying to become muscular but being more phsyically active makes you feel better and your confidence will shoot through the roof.

You can try chat apps like omegle or something like that to practice small talk. You might run into some weirdos though.

How to WIn Friends and Influence People is a good start as far as books. Someone else said No More Mr. Nice Guy which is also good.

there's probably a couple more but eventually self-help books just become mental masturbation. Put yourself out there. Fail. Fail again. Fail more and eventually you'll be a pro.

This, also stay up on current events and there you go.