Bring a large pot of water to boil on high heat.
Peel the sweet potatoes with a hand peeler.
Dice the potatoes into chunks and place them into the pot. Cook the potatoes for 20-30 minutes, or until the potatoes are fork tender.
Drain the potatoes over a colander, and place the potatoes in a large mixing bowl and mash them with a hand masher or electric beater.
Pour the milk, butter, vanilla extract, cinnamon, nutmeg, salt and pepper into the mixture and continue mixing until creamy.
Preheat your oven to 375 degrees Fahrenheit.
Make the crumble topping. Roughly chop the dates, pecans, and pepitas, and transfer them to a mixing bowl. Add the almond flour and butter, then mix thoroughly with your hands until combined.
Spread the sweet potato into an even layer in a 9 x 13-inch baking dish. Then sprinkle the crumble mixture on top.
Bake for 25-30 minutes, or until the top is golden brown.