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How to not be scared to approach women?

I tend to be very nervous around girls that I think that are pretty. A lot of times I fail when it comes to get past the dating phase. One of my main problems is never knowing what the heck to talk about, whether when approaching or on a date. Also I get very nervous when trying to figure out where to take a girl on dates. I need help on how to be more successful with women on dates and what to talk about when I see a girl that I like and want to approach?
How to not be scared to approach women?
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