Prepare the piping bag and count out a few mini chocolate chips before making the shakes. You need only the chips that make the little faces, so keep the rest protected rather than trying to use the whole allowance. Blend the ice cream, milk and vanilla briefly; a longer blending session also lets the mixture warm and lose some of its thick serving texture.
Pour into the two specified large glasses with room above the shake. Pipe the cream upward to make the peak, then place the chips without pressing through the soft mound. Serve immediately with spoons available. If a face is crooked, leave it playful instead of repeatedly handling and flattening the whipped cream while the drink waits.
Timing and servings are estimates. Equipment, ingredients and portion sizes affect the result.