This is all so confusing to someone like me with no skills whatsoever, who lacks confidence and courage. I know it's dangerous to admit things like that on the internet but I'm used to the derogatory comments from both men and women. I am smart and successful in my career, but that's hardly uncommon anymore and not something that makes one attractive in a brief conversation.
I think Calgary Cowboy said it best earlier in this thread:
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How is a guy supposed to know ahead of time if providing attention is 'wanted' if him asking or attempting to 'pick-up' is considered sexist and harassment?
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The last thing I want is to be considered a creep who is being sexually harassing. And considering I'm not a GQ model, I suspect nothing I could venture saying would prevent that. I'm sure the automatic thought is "Great, another loser trying to get into my pants." Considering I've never seen you before, have never heard you speak, and know nothing about you, there is little to go on other than appearance and the current context of the situation.
The very few dates I've ever been on have come through structured settings like online dating or speed dating, where no one is under any illusion as to the purpose.