Melt the chocolate and coconut oil together either over a double boiler or in the microwave in 20-second intervals, stirring until melted.
Add the chocolate to a bowl or a small shallow plate and dip the top of the glasses in, turning to coat the rim. Transfer to the fridge to allow to set.
To make the mocktail, blend the milk, vanilla, and strawberries together until totally liquid. Place a fine mesh strainer over a bowl and pour the strawberry milk over to strain out the strawberry seeds.
Return the milk to the blender and add the coconut milk ice cream. Blend until smooth.
Pour the mocktail into the chilled glasses and serve chilled.