Step 1: Heat a grill pan over medium high heat and add pineapple slices in a single layer and cook 5-6 minutes per side, until dark char marks appear. Set grilled pineapple aside to cool.
Step 2: Combine 4 cups hot water and sugar in a large pitcher and stir with a whisk until sugar dissolves.
Step 3: Process pineapple and lemon juice in a blender until smooth.
Step 4: Pour pineapple mixture through a fine mesh strainer into pitcher with the sugar mixture. Stir well until blended. Serve with ice.
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