Make the dressing. In a bowl or jar, whisk together the olive oil, orange/grapefruit juice, maple syrup, vinegar, Dijon, salt, pepper (and optional garlic) until the dressing looks creamy and blended. If it separates, just whisk again (or shake in a jar) right before using.
Soften the kale—no massaging needed. Add chopped kale to a large bowl. Drizzle about ¼ cup of the dressing over the kale and toss until evenly coated. Let sit for at least 15 minutes (or up to a few hours in the fridge) while you prep everything else.
Roast the squash. Preheat oven to 425°F. Mist a baking sheet with nonstick oil spray, and add the butternut squash in a single layer. Liberally mist the tops with more oil spray and sprinkle the salt, pepper, and optional smoked paprika or cinnamon over the tops. Roast for about 25 minutes, until fork-tender.
Assemble. To the softened kale, add the warm roasted squash, pistachios, pomegranate arils (or other fruit choice), and shaved parmesan. Drizzle on more dressing as needed—or serve extra dressing on the side so everyone can add their own.
Notes
• Trick for softening the kale leaves: Letting your kale sit in a little dressing before building your salad softens it beautifully (without any hands-on massaging. Let it sit for 15 minutes, but up to 3 hours works too!• Storage: Salad keeps up to 3 days in the fridge. For best results, store extra dressing separately.• Vinegar swap: Apple cider vinegar is my go-to here, but champagne vinegar or white wine vinegar work beautifully too—they’ll give the dressing a slightly lighter finish.• To make this a heartier, protein-filled meal: Add chickpeas, edamame, or beans (white or black). And you can also top with grilled chicken, salmon, or tofu. Try my Crispy Baked Garlic & Ginger Tofu!• Gluten-free: This recipe is naturally gluten-free.• Vegan: Skip cheese or use dairy-free parm/feta; the dressing is already vegan when you use maple syrup.• Nutrition: If enjoying additional dressing, add 50 calories per extra tablespoon.
Nutrition information is calculated using a leading industry software. That being said, brands can vary, and there may be slight fluctuations in the numbers.