If your dates are very firm/dry, add to a bowl and soak in boiling water for ~5 minutes. Drain before using.
In a high-speed blender, combine the dairy-free milk, dates, peanut butter, vanilla, and salt. Blend on high until smooth and only small flecks of dates remain. Taste and adjust, adding maple syrup for additional sweetness (we added 1 Tbsp) or more salt for a more salty-sweet balance.
Divide mixture between popsicle molds (we used these) and freeze for ~6 hours, or overnight. When you’re ready to add the chocolate shell, line a plate or baking sheet with parchment or wax paper and make sure there is room for it to fit in the freezer. Let the popsicles thaw slightly at room temperature while you prepare your chocolate shell.
Add chocolate chips and coconut oil to a pint-sized glass jar (or small heat-proof mixing bowl) and microwave in 30-second increments until fully melted and creamy, stirring occasionally to aid in the melting process. Alternatively, melt over a double boiler on the stovetop. We melted the chocolate in a jar for easy dipping/coating!
Carefully remove the popsicles from the mold one at a time, running the mold(s) under warm water if needed to help loosen the popsicles. Working quickly, dip the popsicle in the jar of melted chocolate, tilting and rotating the jar as needed to evenly coat the popsicle. Lift the popsicle and let excess chocolate drip off before placing the popsicle onto the prepared plate/baking sheet. Repeat with remaining popsicles. You can also drizzle/pour the melted chocolate over the popsicle if not using a jar.
Return the bars to the freezer for 15-30 minutes to refreeze slightly, then enjoy! Leftover bars will keep for up to 1 month in the freezer. We recommend storing them in a container with parchment paper in between bars to prevent sticking.
Notes
*Nutrition information is a rough estimate calculated without optional ingredients.