Combine milk and pudding mix in a bowl and whisk or mix until smooth.
Add rum, lime juice, and pineapple, and stir well.
Fold in whipped topping. Once the mixture is smooth and uniform, divide it among 8 small cups.
Place the cups in the refrigerator until ready to serve, at least 30 minutes.
Garnish them with pineapple wedges and lime slices, if using. Enjoy with a spoon!
PER SERVING (1 pudding shot): 90 calories, <0.5g fat, 188mg sodium, 15g carbs, 0g fiber, 8.5g sugars, 0.5g protein