Muslim up-bringing here as well, but the polar opposite. Really interesting to hear you say that though. What makes you think or feel you're out-matched? I reckon if you go in feeling that way from the off-set, you've already lost. Idea is to just be apathetic about the consequences or any potential failure/rejection, and just enjoy yourself and the company.
I'm one of those overly confident or social types who just talks to everyone and anyone (male and female) I bump in to during every day life. Be it a cashier, someone waiting at the tube stop beside me, at an event, shopping, sitting beside me at a restaurant etc (so long as their conversation is interesting, I have no qualms about telling them I've been accidentally nosey and find the convo fascinating). End of the day if you're generally interested and don't want or expect anything in return, I can't see it going too badly.
