Transitioning into comfort is synonymous with transitioning from stranger to 'guy I know'.
You get there by giving the girl an opportunity to get to know you, and vice versa. If you don't make an attempt to get to know her, it may appear that the only reason you're talking to her is because of her looks.
Some examples?
"Where are you from?" "What's the weirdest or coolest thing about <city>? Come on, every town's got at least one thing going for it!"
"What do you do for a living?" If it's a career, "How'd you get into that? Wow, interesting." If it's a stepping stone, "So what do you want to end up doing? Are you doing anything to get there?" (I personally like to weed out bums, and the fact that I ask that shows that I have standards beyond looks.)
"I had the strangest thing happen to me not too long ago..." "Have you ever had anything crazy like that happen to you?"
"Like, Oh. My. God. Look at her butt! You'd think she'd have to get the jaws of life to pry herself out of those pants!" (j/k

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