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I too have this problem of realizing after the fact that I've screwed up. However, I found it helpful to really think about each response and question myself:
1) What do I want to get out of this message? It depends on the situation, but sometimes it's turning the tables when she's trying to take charge, not giving in to cualification or whatever.
2) What do I, based on (1), want to say with this message?
3) What am I actually saying with the message I'm about to write?
4) What will come out of it?
If you're happy with the answers to all question, then send. Else, come up with something better.
As for your last question. Yesterday I had some sucess turning a dull interaction around by making her qualify herself. The technique I used was to state that the way she interacted with me really didn't make the cut, and then handle her arguing responses pretty much like how you'd navigate through shit tests. I finally got her to qualify herself, and throughout our discussion I kept saying that I think there's this fun, adventurous girl (qualities that I want to get out of her, more likely to lead to sex than if you bring out her gentle nice qualities) inside her, "just bring her out for me cause I can't see her right now". Be hard on her, but a bit tongue in cheek. Show her that you're not interested in monotone conversation, you're an adventurous guy!
Yes I know exactly what you mean. Or even saying shit like "well...I;m not even sure if you're my type yet.." sort of speak, you get what I mean. Anyway, back to my story...I fucked up. I stopped at work tonight and this girls cousin was working and she jokingly asked "..and WHY are you talkin to my cousin online dude?" lol I kinda paused and was like "whats that..." She says (again jokingly) "yea...she said you sent her a freinds request and you guys were talking, she said your kinda creepy..."

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When I heard that, it was like a knife in my heart...yea yea call me a wuss, but it really bugged me. I know the MOTTO is "FUCK HER...NEXT!" Right? It just really got to me and made me feel so belittled, like what the fuck did I say...maybe it was my photos in general, who the fuck knows. But I waited a min after she said that and said "pfft...not worried, i doint think shes my type anyway..."