The last two girls who told me they wanted to go on a date with me rejected me. Since those opportunities didn't pan out, I'm thinking maybe I should start approaching women who don't show any signs of interest. Should I bother approaching a woman who doesn't give any signs they'd like to be approached?
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Yes, you should approach her and chat her up awhile. Start formula introduction, notice something about her clothes or whatever attracted you to come speak etc. She will be wondering why SO it has to make sense. Give a good reason for reaching out.
No, if your instincts are good. Yes, if they are not so good as you might really be wrong in the beginning and get a nice surprise.
No pain, no gain, as the saying goes.