Funny thing is the last woman I did approach like that, when I was at the store, wound up being a prostitute. What does that say about my taste in women? LOL.
Back when I was very bad with women, which seems like a lifetime ago even though it hasn't been that long, I dated a stripper and I was very upfront with her despite being very nervous. I did not know she was a stripper initially but I'm a sharp guy so I figured it out. I also figured out she had a boyfriend. Kind of a nutcase.
I believe if this is something you're typically shy about you unconsciously land yourself in situations with women who are "damaged goods". The preceived lack of confidence doesn't bother them and or you can't help but sense they won't mind forward requests. If you're desperate or have trouble communicating sex to women I think you kind of condition yourself to go for wounded prey. If the topic of sex intimidates you or you're unsure of the reaction it'll get from women, naturally desperate women will be the only ones to encourage the discussion.
Really you have to identify your own behavior. For example, do you ever tease, or be playful with a woman? Do you ever tell a beautiful woman who is annoying that she is annoying, even in a humorous way? Jokes are a great form of communication. Poking fun at someone. These things can be done in a way that's not demeaning or rude. I think it you're very serious about your life there is a tendency to have a heightened sensitivity and sense of insensitivity. That sense that many taboo subjects, particularly those outlawed in television and comics for the sake of children, will offend everyone. In real life most of us have lived a little darkly.
Shoe on the other foot. This supposedly virgin girl named Kate used to occasionally Facebook me messages telling me I was cute, that she loved me, etc. Really weird because she almost never talked to me or anyone. She could've been messing with me but I highly doubt it. I am still weirded out by it. The reason I never responded and blatantly ignored her is because she didn't get it. She was a virgin, conservative Evangelical Christian who never dated anyone until recently. I would've been fine if she came and shot the sh** with me, but she never built up the courage to really. I think she would've find her love to me to be a bit of an illusion because she really didn't know I was an atheist, who blasphemed God, hated religion and had a shelf full of Harris, Dennett, Dawkins and Hitchens. She didn't know I recreationally used drugs. I'm not really ashamed of any of it.
That's the point of 'not assuming'. I don't discuss all my business everywhere I go in the real world for very legitimate reasons. Girls like Kate couldn't understand my dark sense of humor, probably would break down in tears if I hassle them about their appearance, or could not say the word penis without giggling. That guy is a very real and fun person, who I'm never apologizing for.
Girls are the same, and they like respect and good manners WITHIN REASON. They don't have to be talked to or coerced like children. If she's with her parents their are manners associated with that exchange. If you bump into a girl in a grocery store its okay to have some conversation besides some robotic conversation about weather. You're trying to turn someone on to you, so what you say should be your unique thoughts, not a forgetable routine.
), but compared to me, he probably thought he was floundering. So he friend-zoned me. 
