Preheat the oven to 425º F.
On a baking sheet, toss together the squash, chili powder, salt, black pepper, and 1 tablespoon of olive oil. Place in the oven and roast for 20-25 minutes, tossing once or twice throughout cooking until the squash is tender and lightly caramelized.
Meanwhile, to make the vinaigrette, add the dates, Dijon, water, apple cider vinegar, garlic, salt, and black pepper, to a blender or use an immersion blender with a large cup. Blend until smooth. Slowly drizzle in the olive oil. Set aside until ready to use.
In a large bowl, combine the lettuce greens, cooked pearl couscous, roasted squash, apples, olives, pumpkin seeds, and pomegranate arils. Gently toss to combine.
Heat 2 tablespoons of olive oil in a medium skillet, over medium heat. Add the Halloumi slices and cook for 1-2 minutes per side or until lightly golden. Remove and drain on to paper towels.
Add vinaigrette to the salad and toss to combine. Top with the fried Halloumi. Enjoy!
