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PREPARE THE BOBA: In a small pot, boil the water on medium-high. Then add the package of boba and stir it in until all the boba balls are floating and boiling. This should take about 3 min. Turn the heat down to medium and continue to stir and boil the boba for 2 min more only.
Immediately remove pot of boba from heat and carefully drain off the hot liquid and put the boba into a separate medium bowl. Pour the cool or room temp water over the boba. Add in the dark brown sugar and stir until it dissolves. This is now boba in its own sugar syrup, which will keep it soft and chewy.
MAKE THE SMOOTHIES: Make the 2 servings of smoothie, either strawberry (or dragon fruit or other fruit of choice), by pouring the milk into the blender first. Then add the ice cubes, frozen fruit, and optional banana. Add in the condensed milk, then the sugar, and blend until smooth.
Taste with a spoon for flavor and adjust sweetness as necessary.
Into the bottom of each plastic cup, put a serving of boba balls. Then pour one serving of fruit smoothie into the cup. Repeat for the second cup.
Add optional whipped cream on top if desired.
Cover each cup with its domed lid and put in a boba straw.