Can a short guy try chatting or flirting with a taller woman or will she consider it weird?

Half_Pint_Guy
If I saw an attractive woman who is much taller then me, what could I do to improve my chances of trying to talk to her? I know mentioning height is a turn off because of showing insecurity but at 5 feet tall, it's also incredibly obvious how short I am.

Ladies, what would you think of a guy my height trying to talk to you if he was otherwise fairly normal looking. (skinny, well groomed, etc)
Can a short guy try chatting or flirting with a taller woman or will she consider it weird?
Can a short guy try chatting or flirting with a taller woman or will she consider it weird?
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