Heat a large stockpot over medium-low heat. Add ¼ cup of olive oil and swirl to coat the bottom of the pot. Once the oil has warmed, add the onion, fennel, and a large pinch of salt. (The salt will help draw out water from the vegetables.) Adjust the heat so the vegetables are gently sizzling, stirring occasionally. Keep an eye on the onions to make sure they don't brown.
Once the vegetables are softened and translucent, add ? teaspoon of curry powder and the chili flakes and continue to sweat until fragrant. Add a quart of vegetable broth and the roasted squash. Season with salt and pepper. Bring to a boil, reduce heat, and simmer, covered, until the broth takes on the flavor of the squash, about 15 minutes.
Blend the squash mixture in a food processor or with an immersion blender until smooth. If you desire a creamier soup, adjust the consistency by adding butter, cream, or an additional ¼ cup of broth and stirring until smooth. Taste and adjust
the seasoning. Ladle into individual bowls and garnish with the chopped dates and toasted squash seeds.
(Just to note, I did not have fennel, used chicken broth instead of vegetable, did not use the dates and used milk instead of cream - and I still found this soup delicious. I did find it a little thin and next time will not add all the broth, but keep some aside until after I put the soup in the food processor or blender and then use it for thinning if I find necessary)