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In a large bowl, whip the cream until stiff peaks form and set aside. You can use either an electric mixer or a whisk.
In a large mixing bowl using an electric mixer fitted with a whisk attachment, beat the egg yolks and sugar on medium-high speed until light and creamy, about 3-4 minutes. Add the mascarpone and mix just until well combined. Add ¼ cup eggnog and mix on low speed until combined and creamy. Then fold in ¼ of the whipped cream. Set aside.
In a small bowl, stir together coffee, remaining eggnog, and rum.
Spread 2 tablespoons of the mascarpone cream in the bottom of a 9" x 7" casserole dish to lightly cover the bottom.
Dip the gingerbread men cookies into the coffee mixture on both sides and arrange about 7-9 cookies (depending on the size of your cookies) on top of the cream. Spread half of the cream on top. Repeat this step one more time.
Pipe the remaining whipped cream on top, cover tightly and refrigerate overnight. Sprinkle with cocoa just before serving. Store leftovers in the fridge for up to 2 days.