Preheat oven to 350 degrees Fahrenheit and add parchment paper to an 8x8 baking pan.
Spread the ⅓ cup and 1 tbs of pumpkin on a plate. Fold a paper towel and pat it dry. Repeat about 3 times and set aside.
Add the butter and sugar to a bowl. Whisk until combined, then add the pumpkin, vanilla, and egg. Whisk to combine.
Add the flour, pumpkin spice, salt, baking powder, and baking soda to the wet ingredients. Whisk until combined. Switch to a spatula towards the end.
Add about ½ cup of chocolate (or more if desired) and ~4 graham cracker squares, crushed up. Fold into the batter.
Add about ⅔ of the cookie dough into the baking dish. Spread evenly. Add the fluff (or if using marshmallows, cut them in half and add them cut side down until all of the dough is covered).
Use a spoon (or cookie dough scoop) to add the remainder of the cookie dough dotted over the marshmallows/fluff. Spread them out a bit, and then add ~2 crushed up graham cracker squares (keep some bigger pieces for the vibes). Add about ¼ cup to ½ cup of chocolate chips/chopped chocolate to the top.
Bake in the preheated oven for ~30-35 minutes, or until the center is mostly set. Let cool for about 10-15 minutes before cutting.