Add frozen banana, cacao powder, almond butter, and almond milk to a blender and blend on low until thick and creamy (see photo), scraping down sides as needed. You are looking for a soft serve consistency.
Add vanilla extract, dates (optional), and a bit more almond milk and blend once more until thick and creamy and well blended. Taste and adjust flavor as needed, adding more almond butter for nuttiness, vanilla extract for vanilla flavor, salt for flavor balance, or cacao powder for more intense chocolate flavor. Set blender in freezer or refrigerator while preparing serving glasses.
Cut a banana in half lengthwise and peel. Then slice in half lengthwise again (so you have four pieces). Slide banana wedges down into two serving glasses (or 1 large serving glass, as pictured // amounts as original recipe is written // adjust if altering batch size), and press with a spoon to “adhere” to the sides.
Add smoothie and top with desired toppings, such as coconut whipped cream, cherries, shredded coconut, and cacao nibs (I highly recommend all!).
Best when fresh but can be covered and frozen up to 2 days. Let thaw before enjoying.
*Nutrition information is a rough estimate calculated with toppings but no dates.