One thing I can recommend to anyone who might have trouble striking up conversations with people (men or women) in general is to go out socially by yourself every now and then. I can't count the number of times I've been out at the bar by myself, struck up conversation with a bunch of random strangers and then proceeded to have a complete blast with them.
Note, this doesn't work very often in Vancouver and Victoria because people out here are #######s.
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