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In a food processor, combine ingredients for the date mixture. Pulse until mixture is crumbly. Refrigerate until ready to use.
For the whipped cream, use a stand mixture with the whisk attachment to combine the vanilla beans, whipping cream and powdered sugar, until mixture is thick (about 3-4 minutes).
In stemless wine glasses, assemble by layering date mixture, whipped cream, berries and caramel. Repeat until glass is full.
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