I've been reading on Vin Di Carlo's Pandoras Box and I was wondering at what point in time of the conversation do I cold read the target?

For instance, for the woman type of a Playette (TDI), here are indirect cold read examples:

• 
  1. There’s something about you that reminds me of myself. It’s like you
  don’t take people very seriously until they earn your trust. But at the
  same time you have fun. For me, I like to hang back and watch what
  people do, and decide who close I want to be with them. Most people let
  me down, so I’m definitely not trying to jump into anything serious when
  it comes to women.
  
  2. There’s something about you…I think you show it on accident sometimes.
  You have this inner sensitivity. When I touch you I can feel a soft warmth
  under your cool, hard shell. I have my walls too, because when I give
  myself to someone, it can be really scary. But at the same time I want to
  because that’s when I feel most complete.
  
  3. I love it when you get silly on me. I wouldn’t take you seriously
  otherwise. Because I’m gonna need your help when I take over the
  world. I’m gonna need someone to give me back massages. Oh and lip
  massages. You have the world’s best kisses. I’ll make you the Secretary of
  Kisses. Just don’t go kissing everybody you crazy girl.
  

I am not completely sure about the Private Dancer, I am actually not really at the right level yet to answer your question.

But I can tell you this:
~ Coldreading the Connoisseur is always a good idea (or at least when you are on chat)
~ Talking about sex with the Cinderella is always a good idea (except when she friendzoned you and knows you use talking about sex to try and connect with her) (talking about sex with her is actually also a bit of a coldread I guess, that's why I am tellling you this)
~ Doing quick and little coldreads on Hopeful Romantics is not a bad idea and forces a little of connection between you. To give you an example:
The girl gets interrupted by a noisy and annoying guy, the girl and the guy engage into a conversation, you interrupt and say to the girl (ignoring the guy and not looking at him) "Ignore him, he has no romantic potential"

Now why is this a cold read?

Well take a look at this prepared and ready-to-use coldread from the PDF:
"I’m definitely open to meeting someone special, but they have to actually
be special – y’know? I think people jump into things before they really
know someone. For me, I have to really get to know a girl and feel like
she cares about me before I have sex with her. Because I feel like I’m just
giving myself away otherwise."

Now take a look at some other text of this book/PDF:
"Ready…Set
The following pages are organized by each of the Pandora’s Box Personality
Types, with three Cold Read examples for each type.

The examples are longer, wordier, and more insightful than is necessary in a
real-world scenario. This is to give you a thorough understanding of what is
going on within each Read, so that you can mix, abbreviate, and improvise
your Reads on the fly.


So what I just gave to you, the example, is according to the PDF indeed a coldread

Okay, I do not really have much more to tell you, but I will figure it out along the way in a while I guess

I am busy exploring the Pandora Box anyways

Please let me know if you have already figured this out and what the answer is