Preheat your oven to 375 degrees.
Cut your squash in half lengthwise and scoop out the seeds.
Drizzle the oil on a sheet pan, and place the squash halves on it, and then toss them around a bit till they are covered in the oil, but ensure that they are face down while cooking.
Roast in the oven for about 30-45 minutes, until the squash is quite soft.
Remove from the oven and allow to cool enough so that you can handle it.
Scoop the cooked flesh out of the shell and toss it in a blender.
To the blender, add the coconut cream, spices, dates, maple syrup and vanilla.
Blend until the pudding is smooth.
Taste for spices and add more if desired.
Place a tablespoon or so of crushed biscoff cookies in the bottom of a pretty glass, and then spoon your pudding on top of it.
Place in the refrigerator to set for about an hour.
To serve, top with coconut cream and additional crushed biscoff cookie crumbs.