Place the buttermilk, pepper and 1 teaspoon salt in a resealable plastic bag and add the chicken, turning to coat. Marinate for at least 2 or up to 8 hours in the refrigerator.
Preheat the oven to 200 degrees F and fit a wire rack in a small baking sheet.
Heat the oil to 375 degrees F in a heavy-bottomed pot.
Whisk together the flour, granulated garlic, paprika and remaining 1 teaspoon salt in a dish. Remove the chicken from the buttermilk and dredge it in the flour mixture. Shake off the excess and, working in batches, fry the chicken until golden brown, 3 to 4 minutes. Transfer to the rack set in the baking sheet and keep warm in the oven while you finish frying the remaining chicken.
To build the bowls, place some shredded lettuce in the bottom of the waffle bowls. Divide the hot popcorn chicken among them, then top with the quartered cherry tomatoes and more lettuce. Drizzle with the Buttermilk Honey Dressing.
Buttermilk Honey Dressing:
Mix together the mayonnaise, buttermilk, mustard, honey, dill, granulated garlic and black pepper in a small bowl and season with salt.