... how do you reach the point when they're comfortable with you and actually enjoying the conversation

Create a comfortable SPAM and an enjoyable conversation?

You don't do this with one sentence or word. You remain comfortable because that will make her comfortable, and you keep the conversation light-hearted, try to keep things flowing, and find something that she's interested in that you guys can talk about. The earlier you can do this, obviously the better. This is why the majority of people will open indirectly - there is no interest being shown and the girl can be comfortable.

"opinion something how old should a child be before they can keep pets?" (shrug)
"fluff"
"neice wants a hamster/rabbit/kitten but i managed to lose 3 hamsters when i was her age"

Pets/animals are a generic winner.

_________________

I'm a winner - I am going to win.

If you've got loads of proximity you can reach the hookpoint very fast. Though usually you will notice when it's time to sit down with the set (or stand closer to them).

It's easy to notice because it will just feel odd to stand beside them, when you're actually engaged in a real conversation.

How to reach that point is kind of simple: open. You should reach it after the opener, or perhaps with some DHV story direct after the opener.

understood

That's usually not the case, especially in Night Game situations.

The key is to plow/persist. RSD calls it plowing and Gunwitch calls it persistence. It's the same thing.

Mystery says that if you say 1 interesting thing, people will say "that's interesting," but if you say 10 interesting things, people will say "you're interesting." There's your hook.

Watch for their body language too; If they are totally into what your saying, you will be able to tell.
And dont dumb down your stories with pointless filler info. Go from point to point, and tell them with emotion.
It doesnt matter what your saying, it just matters how you tell it.

_________________
--Brad