Soak the pitted Medjool dates in hot water for 10 minutes. Drain.
Blend the dates, vanilla, and nut milk until completely smooth.
Slice 2-3 apples into approximately ½-inch slices. Slice to the left and right of the stem so the slices are sturdy enough for the popsicle sticks.
Use a knife to make a small slit at the bottom of each apple slice. Insert a popsicle stick through the slit.
Dip each apple slice in the date caramel, tapping off the excess.
Use a spoon to cover each caramel-coated apple pop with melted chocolate. Tap off the excess chocolate.
Place on a parchment-lined baking sheet and immediately add your toppings.
Refrigerate until the chocolate has hardened. Enjoy!