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The question is a little vague, but I'll do my best to address the topic.
Short crust pastry (I'm assuming you mean like a pie dough or shortbread cookie dough--a dough with lots of butter and no leavening agent like yeast, baking powder, or baking soda) is flaky for the same reason a croissant is flaky--lots of butter. Little flecks of butter are interspersed with flour in the dough, and when the dough is baked, the moisture in the butter evaporates, leaving little pockets of air, which creates a flaky texture.
As for the rolling issue, there could be many reasons that your dough is not rolling easily. I usually use an all-butter dough, which has the loveliest flavor (in my opinion) but is a bit more difficult to roll than a dough using butter and vegetable shortening (like Crisco) in tandem. If you're using all butter, you might try using part butter and part shortening.
It could also be an issue of gluten developing in your dough, thus making it difficult to roll without it springing back with each pass of the rolling pin. Make sure to knead the dough minimally. In fact, when you add ice water to your flour/butter mixture, stir it in only until the dough just barely comes together and is still shaggy looking. Then, let the dough rest in the fridge for at least an hour and up to 24 hours.
When you roll the dough out and place it in your pie dish (or whatever kind of dish you're using), let it rest again in the fridge for about 30 minutes.
Also, I like to add a tablespoon of white vinegar to my dough (that's for a double-crust quantity of dough). This helps to prevent gluten formation.
I have also experienced a remarkable difference in dough straight out of the fridge and dough that has been allowed to sit at room temperature for 10 minutes before rolling. Allowing the dough to warm up very slightly makes rolling a breeze.
You should also beware of sticking when you roll out pie dough. Be sure your work surface is lightly-, but well-floured and that after each pass of the pin, you rotate the dough slightly to ensure it is not sticking.
Finally, if you have an issue with the dough cracking as you roll it (I find that a combination of letting the dough sit 10 minutes after being refrigerated, and making sure the dough is in as perfect a disc as possible works wonders on this front), simply patch the cracks with extra dough. I have seldom, if ever, seen a perfect pie crust. Revel in its delicious imperfection.
Great response and lots of good tips! I wonder if the problem of "flaky and won't roll" could be describing "crumbly and won't roll"? If so, it could be due to improper measuring of the flour and / or not properly cutting in the fat.
Weighing the flour is easier and *far* more accurate than using a cup measure, but if you insist on using cups, scoop up the flour from the bin and strike it level with the back of a knife.
The fat needs to be *cold* and worked into the flour just so -- not too much or the flour won't hydrate properly. I use a food processor, I freeze my fat (half butter, half lard), and I cut it in until the remaining lumps are about the size of peas.
Not a long answer here...butter
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Well played. You deserve a cookie.
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