Opening Up

Here is a problem I have been hearing men having lately: they get into this dynamic where the woman isn't contributing anything, and while she is participating, she is forcing him to do all the work in the conversation. It ends up being very one-sided and eventually the man gets sick of it (and isn't getting anywhere anyway), and he just gives up.

The stereotypical form is the dreaded question-loop:
PUA: Are you from here?
HB: Yup.
PUA: Cool, me too..
PUA: ... so what do you do?
HB: I'm in retail.
PUA: Do you like it?
HB: It's okay.
PUA: Um.. so do you have any pets?
HB: No
PUA: I gotta go find my friends.

The problem is that the man is providing the topic, but asking the woman to provide all the content. The man is not offering up anything personal, but is asking the woman to give personal information. The woman sabotages the conversation (deliberately or subconsciously) by giving one-word answers, so as to end the interview.

The problem is that you need to open up first. Divulge something interesting and somewhat personal, such as your own opinion or philosophy on something. It doesn't have to be deep, but it does have to be something about you.

The weather is supposed to be a no-no, because it's a pretty boring subject, but if you make it personal, it can be good. "You know, when it gets like this it reminds me... you know the thing that I like about the rain is that it feels like home. That feeling right before it's about to rain... you know, that smell.. I sorta miss it because ever since I moved to Texas, I don't really experience it very often." This is not really about the weather at all. It's about my feelings.

Then, when they see you're able to open up, they will feel comfortable talking about themselves.

Talk about yourself (first). Talk about your feelings and opinions and outlook and what makes you tick. Avoid talking about facts that don't convey character, such as what school you went to or what car you drive or what profession you're in, unless you can relate it to your character.

Then ask open ended questions (second). Don't ask her to open up more than you have opened up already. If you've taken the initiative, then it is perfectly fair to expect her to respond in kind.

Avoid talking about third-person stuff. Not that it works against you, but it doesn't help to establish a connection between the two of you. The blue whale is the largest animal to ever live, and you may have thousands of very interesting third-person facts that can keep her entertained for quite a while. But it demonstrates only that you are knowledgeable and very little about who you are. So I find it to be a waste of time in terms of establishing a relationship.

A lot of this stuff is paraphrased from stuff that Juggler teaches. I highly recommend his materials for general conversation skills.