How to connect to someone on a deeper level?

Well I know at my age I should know this, but I have yet to really hone in and actually get to a deeper level with women. I should say I am not a big talker, and the reason why I say this I am always in my head hoping that I don't want to say something "stupid," I don't know much about what they're talking about, or in my head for something else (grooming, dressing, do they find me "hot", etc). When it comes to trying to connect with someone I am interested in, I realized that I tend to keep things on the surface level. I really don't know how to connect on a deeper level, and flirt.

How to connect to someone on a deeper level?
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