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Am I playing it too safe with women and blocking my own dating chances?

I've been single my whole life because I've always played it safe with women, hiding any interest or trying my best not to confuse flirting with being nice and that usually leaves me confused on how women feel about me. The only guarantee time I'll flirt with a woman is if she's throwing very clear signs she's interesting in me but that's basically the rarest thing to think of for me.. I'm not the worst looking guy, I'd say maybe a strong 6. I'm 6'3, always been told I'm funny but it has never lead to anything.. what can I do about this?

Am I playing it too safe with women and blocking my own dating chances?
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