Ensure that any pineapple you have has been frozen, or it could mean disaster.
Place all ingredients together except the pineapple wedges into a blender. This would include the pineapple, pineapple juice, and sugar (or sugar substitute/sweetener).
Limit the amount of ice you add to the blender - especially at first. Although you want a frozen dessert, you can easily prepare a dessert with a lot smoother texture than the Disney Parks dole (sorry for the pun) out.
Pulse the blender. You will want a dessert a little thicker than smoothie-like, but less than frozen solid with chunks all over. The whip should still be that off-white color when it finishes.
Find the right consistency of the pineapple-pineapple juice and sugar/sweetener. While you can add ice for a little firmer texture, you won't want to add too much.
Take off the blender's bowl and pour all contents out into a mug or two. If you have a hollowed-out pineapple half, use that instead.
Garnish the dessert/mug. Make a slit down about the middle of the pineapple wedge. Place the wedge over the edge of the mug down into the Dole Whip.
Serve cold. Frozen is best, but very cold is ideal. The colder, the better.
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