Preheat the oven to 350 degrees F. Add the tomatoes to a lined baking sheet and drizzle with 1-2 TBS olive oil and a healthy pinch of salt and pepper. Mix up to fully coat them, then roast for ~15 minutes, or until the tomatoes are slightly shriveled and tender. Set aside.
Bring water to a boil. Once there, add a big pinch of salt and the orzo. Stir, and then let cook per the package instructions. When done, reserve ¼ cup of the pasta water, drain the orzo, and set aside.
While the orzo is cooking you can begin the aglio e olio. Add the extra virgin olive oil and garlic to a skillet. Allow to heat together or medium-low heat so that you DO NOT BURN the garlic. Moniter the heat and lower it if necessary, stirring often. This takes ~5 minutes.
Once the garlic softens, add the lemon juice and red pepper flakes. Note that the garlic can turn a light brown color. Do not let it go beyond this. Cook for ~3 minutes, then add the orzo and pasta water, and stir to coat in the garlic oil.
Add the tomatoes and basil. Taste and add salt and pepper as needed. Serve immediately.