I'm on some kind of "dating site" where a guy can get away without putting his picture up, and still get some replies from women. That's part of the climate of this site. As long as you write a good copy--since the majority of guys on this site do not, or otherwise they write creepy shit--you can stand out enough to get replies.

The initial reply I will get from women is they'll mention something I put in the ad, or have a question about something I said. It's usually a 1-2 line reply, and sometimes just "Hey how are you?" It's what I say next that's the problem. Lately I've had 4 conversations that all seemed to stop very quickly... barring the possibility that they're busy, I want to know if I'm doing something wrong.

I've been taking the "don't think too much about it" approach.. using my normal intuition to reply back to them. I used generally the same thing for all of the 4 conversations: "So, what part of the area are you from? I'm from (my town)"

It's an intuitive next response for me because: 1) The idea is not to fool around in email for long, but to meet up with someone, and it helps to know what general location they're located in 2) It's a decent topic for conversation

What else am I supposed to say? I don't even know what these women look like, and I can't always think of some witty crap to say, especially when they don't offer anything up in their reply. When they do open up with something witty, like: "You must be a unicorn, you don't exist," I'll give them a witty reply back and the conversation continues, but at some point I need to know something about these women.. so I ask a basic question, and that's where it stops.

How else am I supposed to do it? Am I not supposed to ask questions? WTF.

TL;DR After I get a reply to my profile, the next thing I usually do is to ask "tell me a few things about yourself.. what part of the area are you from?" and the conversation dies immediately. Why is this?