bluemoon, the problem isn't the "low value girls" IMO, it's your mindset.

You don't feel valuable enough to even entertain this girl you've got an IN with, and so you're calling her fat as an excuse.

Deeper issue, which is fine. It's good to nail it on the head, and this is the perfect place to do it.

Inner game, man, inner game!

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- Zip

Hey man,
Don't put yourself down trying to entertain a girl,
I used to take girls to the same restaurants until I realised that bowling and pool were much more fun places to take them especially since you can talk while your there!
Don't call her fat also, you asked her out so this wasn't a factor then and it is only reflecting on your insecurities and low inner game!
If your positive, she will find you incredibly attractive!

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You miss 100% of every opportunity you do not take

No, I've tried going out with women I'm not really attracted to, just to get experience or whatever, but I can't even muster up enough energy to interact with them. I just don't see the point of it. You can't learn to do what you like by doing what you don't like. It doesn't make any sense.
I'm open to ideas, but I don't think your analysis quite hits the mark. But you don't know me so that's perfectly forgivable.

One of my key goals is to be the selector of the woman, rather than having something easy-but-less-than-ideal come along and settling for that. I'm tired of that, not to mention that it's totally emasculating.

Take her on a balloon ride, if you can't afford it well then get your life together and start attracting some wealth to your life. You can't just be good with the ladies and get by forever. You gotta also have wealth and health stacked along with the love to be happy. If you were confident you wouldn't be wondering, be the prize amigo. Have her plan out the date to really give urself some value. =P