Stir all ingredients in a bowl and fill the popsicle molds halfway full. Stick them into freezer for about 20-30 minutes.
Meanwhile, make the date caramel.
Put about 2 tablespoons of date caramel in the popsicle mold. Sprinkle with a few chocolate chips if you like! Be sure to push down the caramel all the way down to the vanilla yogurt ice cream. Put the popsicle sticks into the mold at this point as well. Then, freeze for about 20 minutes. Fill the remainder of the popsicle mold with the vanilla yogurt. Freeze again for 3-4 hours.
Next, you can remove the popsicles from the mold by running warm water over them. Gently slide them out and place on a parchment lined baking sheet. Place back into freezer for 20 minutes.
Meanwhile, melt chocolate chips in a mug.
Remove popsicles from freezer and quickly dip into melted chocolare. Return to freezer until set.