| I've been having similar problems but recently I've started making small breakthroughs so I will share some of what I have learned. It's not the perfect fix but it will get the ball rolling and hopefully you can share your experiences.
I haven't structured this yet and it's a collection of ideas from all over the net but I have made small notes. when I get time I might actually re-write the whole thing.
Always have a goal of what you want to achieve and work towards it. Are you just making small talk from boredom? after her number? a meetup? without a goal your not going to achieve anything and therefore the entire thing is pointless.
Adopt “Question-Comment-Statement” to Avoid Interview Mode
ask more probing questions such as:
“What do you like about that?”
“Why did you decide to do that?”
“Why are you doing XYZ instead of ABC?”
“If you could do anything else instead of XYZ, what would it be?”
"How long have you been doing that for?"
"How do you like it?"
"Do you think you'll [get promoted / move up / open your own business / master that hobby or art]?"
"If you don't like it that much, why are you still doing it?"
"How'd you get into it if you don't like it?"
"Think you'll do it forever?"
"What's stopping you from doing it?"
Each of these questions gets you deeper into finding out more about her - and keeps her talking more.
“I've neverbeen to portland.. What's it like, and why did you leave there for here?”
“Really? My friend works there too. What do you like better, being around college kids all the time or getting to work in the middle of downtown?”
He's given her a couple of interesting options for telling him about what she likes.
Throughout your conversation, you'd be well advised to provide feedback to show that you're paying attention and relating.
Just little remarks like:
"Hmm."
"Oh I see."
"Really?"
"That's crazy."
"How'd you get through that?"
"That's pretty remarkable."
"I'm surprised you hung in there that long."
... and others like those are all you need. These offer encouragement to her to keep talking, and keep going with the topic.
Statements and comments such as these help give ideas of how to keep the conversation going.
“I imagine…”
“When I came in I imagined girls out front fighting. It seems that sort of place. I don’t know about you but I have to admit I’d kind of like to see that.”
“That reminds me…”
“I don’t know why exactly but that reminds me of my trip to Japan. I found the people like you, open to new ideas in a way that I found inspiring.”
“I don’t know anything about that but I’m guessing it’s like this…”
“I didn’t grow up playing rugby, I’ve never been to a match, but I imagine, from how you talk about it, that there’s a great camaraderie among players, that you might be enemies on the pitch but off it you’re friends.”
“I can’t relate to XYZ…”
“I can’t imagine how you felt. To walk in on your boyfriend
“I want to be…”
“No, I’m not in a relationship but one day, when I meet and pick up Anne Hathaway, I want to be.”
“Let’s pretend…”
“I think we should pull off a caper like in that movie Oceans 11. Let’s pretend. I think you can be Julie Roberts character because you’d look stunning in a cocktail dress. I get to be George Clooney because it’s my idea.”
“… just kidding..”
“This is normally where I would try to impress you but I’m not.”
Turn It Back to Her. Your conversations then will look like this:
Her: ... but anyway, that's me! What do YOU do for fun?
You: Me? My life's so BORing, I hardly do anything for fun. I just work all the time. You said you like playing billiards... are you any good?
Her: I'm not bad. Well if you work all the time, what are you working on?
You: I'm a sculptor; I make statues. But it's not as exciting as it sounds, it's really just sitting in front of a block of granite all day with a chisel in your hands.
Her: Wow, that's so cool!You: Do you do anything artistic?
Her: I don't, but I've always wanted to be an artist! When I was little, I...
Drop in some cold reading. this gets her curious as to what you think of her and she will try to investigate by asking questions.
Make a statement about her and then leave it unfinished so she tries to get this information out of you. She is the one then pursuing you for conversation to satisfy her curiosity.
e.g. "I don’t know if anyone has ever told you this before, but I just noticed something really interesting about you" and then go on to talk about something completely different.
make it seem like you know something that she doesn't. try and turn the conversation so she is qualifying herself to you. by making statements such as.
"Hmmm I'm not so sure"
" and you were doing so well... now you've just lost 10 points"
"ahh you don't wana know!"
"you couldn't handle the truth"
it sets the frame so that you are the chooser and she will start prving herself to you.
I realise this is far from perfect but it might get the ball rolling.
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CHAT