Prepare pudding in a large bowl, according to package instructions, mixing in milk.
Scoop pudding into clear cups or shot glasses and chill for at least 5 minutes.
Top each pudding cup with crushed Oreos.
To make the strawberry ladybugs: melt 1 cup chocolate until smooth.
Dip bottom tips of each strawberry half in chocolate to make the ladybug face.
Lay on parchment paper to dry.
Next push 6 mini chocolate chips all over each strawberry.
Top each pudding with one or two ladybugs.
Serve with a spoon for digging into the dirt!