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Iceberg Wedges with Grilled Bacon and Croutons

['1/2 cup buttermilk', '1/2 cup sour cream', '1/3 cup finely chopped mixed fresh tender herbs (such as tarragon, chive, parsley, and/or dill)', '2 tablespoons fresh lemon juice', '1 garlic clove, finely grated', 'Kosher salt, freshly ground pepper', '8 slices thick-cut bacon (about 1 pound)', '3 ounces country-style bread, crusts removed, torn into small pieces (about 1 cup)', '1 head of iceberg lettuce', 'cut into 8 wedges']

Whisk buttermilk, sour cream, herbs, lemon juice, and garlic in a small bowl to combine; season buttermilk dressing with salt and pepper.
Prepare grill for medium heat and heat a cast-iron skillet directly on grate. Working in batches, cook bacon in skillet, turning occasionally, until browned and crisp, 8–10 minutes. Transfer to grate with tongs and grill bacon, turning once, until charred around the edges, about 1 minute. Transfer bacon to paper towels to drain.
Toss bread in same skillet until coated in bacon drippings. Transfer bread to grate and grill, turning often, until crusty and charred in spots, about 2 minutes.
Drizzle buttermilk dressing over iceberg wedges and crumble bacon over. Top with grilled croutons.

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