Why is it when I ask out a woman they end up rejecting me? (check comment section for more)

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You should be focused less on accomplishing a goal with a woman, (asking her out) and more on just interacting with her. If you just walk up to a girl, don’t interact with her much, and then ask her out, you’re basically saying to her, “I’m not fun to interact with now, but if we go on this date, I’ll be fun to interact with there.”

Work on being a fun guy for women to hang with, then dating will come naturally from that.