Social retard reporting in, I know it's dumb to ask questions

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Social retard reporting in, I know it's dumb to ask questions concerning social interaction but I'd like some "pointers" anyway.

>How do you strike a good balance between asking questions/making statements ? I don't want to seem like I'm interrogating others but I also don't want to come off as an overly-opinionated narcissist.
>How do you take the initiative (that is to say, begin a conversation) with someone you've talked to before without seeming clingy or desperate ?