Healthy Recipe Jello Pudding Pops from Sports N Fitness 1 package JELL-O Chocolate Sugar-Free Pudding 2 cups Fat-Free Milk 1 cup Sugar-Free Cool Whip 1. Beat pudding mix & milk in medium bowl with whisk for about 2min. 2. Stir in Sugar-Free Cool Whip. 3. Spoon mix into small paper/plastic cups. 4. Insert wooden sticks into the middle of each. 5. Freeze for 4 hours or until firm. - To remove from cups, run under warm water.