In a large mixing bowl, beat cream cheese, pudding mix, and one cup peanut butter until well combined using a hand mixer.
Add milk, ¼ cup at a time, and beat until well incorporated. Gently fold in whipped topping until fluffy.
Fold in chocolate chips and peanut butter cups.
Transfer mixture to a serving bowl. If time allows, refrigerate for at least 2-3 hours, or overnight.
Serve with graham crackers, vanilla wafers, chopped fruit, etc.