Preheat the oven to 400°.
Line a sheet pan with parchment. Halve the squash lengthwise and scrape out the seeds with the edge of a teaspoon. Place cut-side down on the lined sheet pan and bake until the necks are soft and the juice around the edges is foamy and browned, 35 to 40 minutes.
Remove the sheet pan from the oven and let rest for 3 minutes. Gently turn each piece of squash face up. Pour cream into the seed cups to fill, about 2 tablespoons each. Sprinkle with salt and freshly ground black pepper.
Serve immediately before the cream is absorbed or wait a few minutes to hide the evidence.