Realize that 99% of the people you see out in the world you'll never see again. The other 1%, realize you cant please everyone so just be yourself. Whats the worst that happens, they don't like you? Doesn't matter. I always liked the mantra of "Will this matter tomorrow? 1 week? 1 month? 1 Year?" 99% of the world only cares about themselves and yet were all in this together so in the grand scheme of things, a random interaction with someone isn't that important. And if it IS important and they like you and want to see you again, its because they like you as a person.
As to what to discuss and how to influence them? Learn their name (the most important thing to a person is their name). Say it back to them. Also, let the other person talk. They will drop hints of what to discusses. If they're nerdy, talk your nerdy. If they are in school, talk about that. Just find a common interest.
EDIT: To summarize, realize you have nothing to lose and everything to gain.
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https://www.reddit.com/r/AskMen/comments/9qnd7n/how_did_you_become_more_socially_successful/?sort=top
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My whole life I've been extremely sociable and the only reason why is because of two things.
I spend zero amount of time thinking about someone else's opinion of me. When I do focus on that my guard immediately goes up and fear starts to control my behavior eventually cutting me off socially. Focus on all of and only the great aspects of all social experiences life throws your way.
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Let me preface this by saying I'm not trolling.
Every single day for atleast 30 minutes, go out and talk to complete strangers. They can be anywhere and the place you go does not have to be a social setting at all.
Most people can not do this because we are socially conditioned not to. But if we were, everyone would be a lot more keen in this area.
The process is called gradual desensitization. The more and more you leave your comfort zone, the better you become at that thing you were once inept at, or even afraid of.
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