Place the graham crackers in a food processor and process until crumbs. Pour into a bowl along with melted butter and both sugars and stir to combine.

Divide crumb mixture between 10 cups (we used 8-ounce glass cups), and press down with the bottom of another small glass or a muddler also works well.

In a stand mixer with whisk attachment, whip cream to stiff peaks and set aside in a separate bowl.

Place the cream cheese into stand mixer with paddle attachment and beat to creamy, about two minutes.

In a medium bowl, combine cheesecake pudding mix along with eggnog and optional rum. Whisk until combined then let sit for one minute.

Add the cheesecake mixture to the bowl with the cream cheese and mix on low until combined, scraping sides a few times.

Fold in the whipped cream by hand, then place the contents into a piping bag* fitted with a large star tip, and fill the prepared glasses, refilling the pastry bag as needed.

Sprinkle on a tiny amount of nutmeg then top with a cookie as garnish.

(Can be made ahead and refrigerated, however place the cookie for garnish just before serving. The cookie will get slightly soggy over time as it sits in the cheesecake.)