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A Summer's Night Shrimp Cocktail

['3 Roma tomatoes, halved lengthwise, plus 1/4 cup seeded and diced ripe tomato', '4 quarts plus 1/2 cup water', '1/4 cup plus 2 tablespoons freshly squeezed lime juice', 'Kosher salt', '1 1/2 pounds medium-size shrimp, tails removed, peeled, and deveined', '2 tablespoons sauce from chipotle chiles in adobo sauce', '1 1/2 tablespoons honey', '1 small clove garlic, minced', '1 teaspoon Worcestershire sauce', 'Pinch of freshly ground black pepper', '1 avocado, halved, pitted, peeled, and cubed', '1/2 cup cubed unpeeled English cucumber', '1/4 cup chopped yellow onion', '1/4 cup loosely packed chopped fresh cilantro', '1 tablespoon minced jalapeño chile (optional)', 'Saltine crackers, for serving', 'Lime wedges', 'for serving']

Position a rack on the top level of the oven, about 4 inches from the broiler. Turn on the broiler. Line a rimmed baking sheet with aluminum foil. Place the tomato halves on it, cut side down. Broil for 10 to 12 minutes, or until the tomatoes are softened and slightly charred. Allow to cool to room temperature.
Combine 4 quarts of the water, 1/4 cup of the lime juice, and 2 tablespoons salt in a large saucepan and bring to a boil over high heat. Add the shrimp and cook for about 3 minutes, until they are fully cooked. They should be bright pink-orange, curled, and firm but not hard. Immediately drain the shrimp into a colander and hold under running cold water for about 1 minute. Drain well, transfer to a bowl, cover, and refrigerate until cold.
To make the cocktail sauce, combine the roasted tomatoes, the remaining 1/2 cup water, the remaining 2 tablespoons lime juice, the adobo sauce, the honey, the garlic, the Worcestershire sauce, and the pepper in a blender and puree on high speed until smooth. Season to taste with salt.
Pour the sauce into a large ceramic or glass bowl. Add the shrimp, avocado, cucumber, onion, diced tomato, cilantro, and jalapeño. Stir gently to mix.
Serve in tall glasses or sundae glasses with long spoons and accompany with the crackers. Pass the lime wedges at the table.

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