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Make the filling by adding whipped topping, yogurt, peanut butter and maple syrup to a bowl and whisking until smooth and creamy. Set aside.
Open the dates and line them up on a parchment lined sheet pan. Cover with parchment paper and use a rolling pin or heavy pan to flatten them into a large 8x4 rectangle. Cover any holes with small pieces of date and re-roll. Cut the rectangle into two equal 4x4 squares.
Place one date rectangle onto a parchment lined sheet pan, spread the filling over the dates, top with the second date square and gently press down. Freeze for at least 5-6 hours or overnight.
Slice the large square into 8 smaller squares and return to freezer until ready to dip.
Melt the chocolate and coconut oil together in the microwave on 30 second intervals, stirring after each interval.
Dip each sandwich into the chocolate to cover half of it, place on a lined sheet pan, sprinkle with peanuts and freeze for 10 minutes until chocolate hardens.