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Cut away peel and pith from grapefruits and oranges. Cut each fruit in half from pole to pole, then slice crosswise to inch thick. Transfer to bowl, toss with sugar and ½ teaspoon salt, and let sit for 15 minutes.
Drain fruit in fine-mesh strainer set over bowl, reserving 2 tablespoons juice. Arrange fruit on serving platter and drizzle with reserved juice.
Whisk reserved juice, shallot, and mustard together in medium bowl. Add radicchio, ½ cup dates, and ¼ cup almonds and gently toss to coat. Season with salt and pepper to taste.
Arrange radicchio mixture over fruit, leaving 1-inch border of fruit around edges. Sprinkle with remaining ⅓ cup dates and remaining ¼ cup almonds. Serve.