In a small bowl, beat the cream cheese with an electric mixer until smooth. Set aside.
In another bowl, whisk together the pudding mix and milk. Then add the cream cheese and mix with the whisk or mixer until well combined and smooth. Place in the refrigerator for a few minutes to chill and set.
Spoon 1-2 tsps of pudding mixture onto the flat side of a NILLA wafer. Cover it with another one and press down gently to form a sandwich. If the mixture feels a bit soft still, place the cookies in the freezer for 10 minutes.
In a small bowl, combine the chocolate chips and vegetable oil. Microwave for 30 second intervals, stirring well each time. Keep melting and stirring until the chocolate is smooth and shiny.
Holding the sandwiches by the bottom cookie only, dip the tops in the chocolate. Allow the chocolate to drip off, and then gently scrape along the side of the bowl to remove any excess.
Refrigerate once more to set. Once set, serve at room temperature or freeze for later use.
Using cream cheese in the mixture help keep the filling from getting too mushy, especially at room temperature. It also gives it a rich flavor! If frozen, allow to thaw for 15-20 minutes at room temperature to soften a bit. However, these do taste great frozen!Makes approx. 40 cookie sandwiches