Cut squash in half and remove seeds. Place cut side down on a parchment lined baking sheet. (For cubed squash toss with olive oil and place on baking sheet.)
Bake in 350°F oven for 45-60 minutes until cooked through. Allow to cool slightly then spoon squash out of skin. Set aside.
Blacken poblano chiles over a gas flame or under the broiler, turning to blacken on all sides. Place chiles in plastic bag and steam for 10 minutes. Pull as much blackened skin away from chile as possible. Remove seeds and roughly chop. Set aside.
Heat oil in a large pot over medium heat.
Sauté onion and garlic until translucent, 4-5 minutes.
Add chopped poblano chiles and cumin. Sauté stirring until fragrant, 2-3 minutes.
Add squash and chicken stock, bring to a boil and simmer 15 minutes. Cool slightly then puree in batches using a food processor, hand blender or food mill. Return to pot, taste and season with salt and pepper.
To serve as soup shooters - Add additional chicken stock to get the desired consistency. Garnish each shooter with sour cream, toasted pumpkin seeds and fresh cilantro.
To serve in bowls - Make a ring of tiny dots using slightly thickened whipping cream or yogurt thinned with cream. Use a toothpick or skewer to draw a line through the dots creating a heart pattern. Add toasted pumpkin seeds and cilantro if desired.