Preheat your oven to 400°F (200°C). Slice off the top of a whole head of garlic, drizzle with olive oil, wrap in foil, and roast for 30-35 minutes until golden brown.

In a mixing bowl, combine softened cream cheese and mayonnaise. Season with salt, black pepper, and dried Italian seasoning. Blend for 2-3 minutes until creamy.

Squeeze the roasted garlic cloves into the bowl with cream cheese mixture and blend again for 1-2 minutes until fully incorporated.

Fold in shredded Parmesan cheese evenly, ensuring not to overmix.

Transfer the dip to a serving bowl and let sit at room temperature or chill in the refrigerator for at least 30 minutes before serving.