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In a medium skillet, whisk together milk, sugar and corn starch. Cook over medium-low heat, whisking constantly, until thickened, about 8-10 minutes (it won’t be thick like pudding, it is a dressing — but it will thicken considerably).
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Stir in vanilla. Remove from heat and let cool to room temperature (you can speed this up by refrigerating for 30 minutes).
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In a large bowl combine strawberries, blueberries, blackberries, oranges, kiwi, pineapple and grapes. Whisk the cooled dressing and pour over fruit. Toss to coat (be gentle — you don’t want mush!).
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Serve at room temperature or chill to serve later. If making ahead, only add the dressing 1-2 hours before serving.
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