So, I was qualifying this HB9 the other day. We were bantering back and forth and then came the line "you're flirting with me, you like me" so I shot back the standard "well, you're cute and can banter, but what do you have going for you besides looks?". I was waiting for qualification and she said "huh, I've never been asked that. I can't really come up with anything right now".

Thing is, this is a really sweet girl. I know some of her interests and we have commonalities. She also loves children and wants kids, like me. We get along well and aren't at a loss for words. But, since she blew this qualification, I rolled off due to instinct. I KNOW she qualifies for me, but I caught her completely off gaurd or unprepared. Or she has low self esteem. What's my next move?

Chances are you caught her off guard, most HB's 8+ hear the "hot/cute/sexy" etc things all the time so they get used to that, and when you drop a qualifier like "well what else is special about you?" they might be surprised(which IMO is a good thing).

Did she seem put off by it? or just kind of at a loss for words?

If I were in your position right there I would have laughed and said something self-deprecating to pull some of the attention off of her.

I would give her a couple days and then try and hangout again, get a good convo going and try and qualify again, but maybe rephrase it slightly, like "so what's something interesting that people don't really know about you?(or something they wouldn't be able to guess)" or "what's something you think people overlook about you?"
Just something more defined and less open-ended than "what do you have besides looks?", which for most women is ok, but some it might be a shocker

It seems like she was just caught off guard which is almost perfect for you but i would have taken some of the pressure off like arcteryx said

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Thanks for the ideas guys. Rolling off seems to have created mystery, but I know how to proceed now. And Mayhem, that girl in your pic is absolutely adorable. And you can tell she is fucking loving her time with you. If you get the chance with her, I saw win this game with her.

I never was in this situation but what do you guys think about helping her with the qualification ? Let's say like this:

you: What is special about you, besides your looks ?

HB: I don't know how to answer that question. I have never been asked this before.

you: Hmmm, well let me help you out then. From our interaction I spotted that you are fun to be with and playfull, something that I really appreciate in girls because I don't like to hang out with cold boring girls. Besides that my guess is that you are also a person that care a lot of the people you like, like your family and friends. Am I right ?

So basically do some general cold readings on her in order to help her qualify to you. In that way you make her qualify to you, you show her that you were really assessing whether she is good enough for you and that you are good in assessing who she is. I never tried this out but for some reason to me this approach looks even better than the standard qualification procedure. What do you guys think ?