I got HB 7.5 # last weekend. We text a little, then I text her tonight:
Me: "What are you wearing tonight?"
Her: "Excuse me?"
Me: "Tonight... when we get together for drinks at Maxwells? You pervert! What were you thinking I meant?" Her: "I was just confused on why you were asking (laughing smiley) I'm actually going to the Westerner tonight."
Me: "Haha... So are you wearing a sexy red thong?! That's my favorite... Well lets get drinks for 30 mins before you go."
Her: "That's inappropriate. Haha"
Me: "You fucking love inappropriate! Lets get drinks at Whiskey at 9:30. For 30 mins then I gotta go meet my friends."
Her: "Ew. Have a nice night."
Me: "I thought you were cool and confident. Now Im not so sure."
Her: "I am cool and confident. I just don't enjoy being disrespected by guys."
Me: "(HUG) I meant it for fun! I can be a bit of an asshole sometimes. So what makes you cool and confident?"

NO reply.

So I have several questions, but first let me explain some of my thinking. This was the first time I used the "What are you wearing?" to start a text. Pretty scary at first. I think I did well in playing it off when she responded with "Excuse me?" But then I wanted to push it and keep it going sexual and see how far I could go. Plus I wanted to give her the idea that I want her to wear a red sexy thong for me!

My first question: When a girl says "That's inappropriate. Haha" Does that mean that I'm about to cross the line and I should just change subject or whatever? I clearly pushed it too far here and she got upset.

Second question: What are examples of how I could have redirected the text after "That's inappropriate. Haha"?

Third question: When I do push something too far, how do I recover? (Please don't say just move on. I want to up my game to the next level, and while I don't care about this one girl, I believe I have to learn how to adapt to all kinds of situations and calibrate after the fact to pull tons of HBs. So please answer knowing that I come from a mindframe that I don't care to get this one girl. I want to learn to be better.)

I think you screwed up on the last message, hence why she stopped responding. Save the messages for setting up dates - which is how you started out well. Probably asking her to qualify herself over a text though is probably wrong unless she's a submissive little nymph. I'd leave that for in person. Where she doesn't have time to review what she has just said or tried to say. Nobody wants to think so much about themselves. As a matter of fact, she's that cool and confident that she didn't put up with your shit and stopped texting you. Also, too much unreciprocated energy never works i find.

I don't think she was into that at all, dude.

You need to read situations... And you were not at the point to be asking about this girl's underwear, based on how she reacted when you mentioned it.

Move along...

Lol

I don't know who you're listening to, or who you're copying and pasting these text messages from, but that isn't going to get you anywhere unless you have first established an emotional connection with the girl. It sounds like she liked you and were interested in you, but had no idea who it is you were being. Is that personality from the text congruent with the personality you displayed when you got her number? I doubt it. You have to operate from whats congruent with your actual personality as you improve and grow.

It doesn't even sound like you took the time to get to know her. The way she's going to see it is.. " If this guy is talking to me like this through text and he doesn't even know me. What is he going to do once he actually gets to know me. Whats he going to do in person ".

You scarred her bro.

Let her go and be more of yourself next time. Stop following the layouts from these guys on the internet. If those things are working for them its because they've established an emotional connection with the girl first. You don't just come out of know where command a girl come out with you. You could be a killer, a rapist potentially. And based on the timing of your messages I could see how she could think that is possible.

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Yeah what Eddie said. You can't just jump right into it so quickly. It's a super creep red flag. I mean that's pretty much rule #1 almost after getting the number. Texting can be a great weapon. But I've been learning that calling and talking or calling and setting up a date is the way to go. Or at the very least just text minimally and mostly focus on asking her to hang out. Once you go on a few dates, establish a nice report then you can start in a little bit with the flirty sex talk. But even then tred lightly and don't do it every day. Gently, slowly man. Flirt, but flirt about her personality not about her body. So instead of saying "omg your boobs are so big, how do you run?" and you think that's a funny, playful line she'll take it as disrespect and it automatically means you're viewing her as a piece of meat and not a person. Flirt with her personality like "oh man, you're so demanding, you really are a Cancer aren't you?" Or "wow your choice of tv shows is so immature." Playful things about her personality, not her body. That comes later, and is a case by case basis. If a girl responds to that type of texting right away then she's probably a tramp and you don't want her anyway.