Prepare one half of my perfect pie crust recipe according to directions. Form a disk and place into the fridge for at least 30 minutes.
Remove the pie dough from the fridge and on a lightly floured work surface, roll out dough to about ¼ inch thick and about 2 inches wider than your pie pan. Roll the pie crust into the pie pan and be sure to poke the bottom a few times with a fork to allow air to escape during baking. Cut away any undesired excess crust and crimp, curl, or decorate the edges however you like!
Chill the pie crust in the freezer for at least 30 minutes before baking (if you skip this step, the pie crust will shrink). While the crust is chilling, preheat the oven to 425°F.
Place a piece of parchment paper or heavy duty aluminum foil inside the pie crust and fill with pie weights (uncooked rice or dry beans also work great).
Bake at 425°F for 15 minutes. Carefully lift the parchment paper and pie weights then return the pie crust to the oven to bake for another 5 minutes or until the bottom of the crust is just beginning to brown.
Remove from the oven and set aside.
Reduce the oven temperature to 350°F.
Combine the butter, brown sugar, bourbon, vanilla, and heavy cream in a large saucepan over medium heat. Whisk to combine the ingredients and dissolve the sugar.
Bring to a boil and allow to boil for 3 minutes while stirring frequently. Carefully spoon about ¼ cup of the mixture into a glass measuring cup to temper the egg.
Whisk the egg in a small heat-safe bowl and slowly drizzle the ¼ cup of syrup into the egg as you continue to whisk (whisk continuously so that the egg doesn't scramble). Once the egg and ¼ cup of syrup are fully combined and smooth, then pour back into the syrup mixture and stir until combined.
Remove from the heat and stir in the Medjool dates, pecans, and cinnamon. Pour the filling evenly over the par baked pie crust. If desired, add more pecans on top.
Bake for 15-25 minutes or until a toothpick inserted in the center comes out mostly clean. If the top begins to get too brown, loosely cover with foil for the remainder of the baking time.
Remove from the oven and allow to cool completely to room temperature before slicing. Top with flaky sea salt if desired.