Preheat oven to 400°. Toss butternut squash cubes in ½ tablespoon of olive oil to coat, and arrange in an even layer in roasting pan or on a baking sheet. Bake until tender and lightly browned, about 20 minutes.

While butternut squash roasts, place the hot water in a small cup and add saffron. Allow to sit for a few minutes while you begin preparing the rice. The color should begin to run.

Coat the bottom of a medium saucepan with remaining tablespoon of oil and place over medium heat. Add shallot and sauté until soft and translucent, about 5 minutes. Add rice, cinnamon, cumin, and cardamom. Toast the rice and the spices for about 2 minutes, until the spices become very fragrant. Add saffron water, bay leaf, vegetable broth, cherries and dates. Raise heat and bring the liquid to a simmer, stirring a few times. Lower heat and cover. Allow to simmer until all of the liquid is absorbed, about 20 minutes. Remove from heat and allow to sit for about 5 minutes.