How to Make It
Drizzle 1 Tbsp. chocolate syrup down the inside of a 1/4-cup rocks glass, using a squeeze bottle or spoon. Repeat with 3 more rocks glasses.
Process vanilla ice cream, creamy peanut butter, whole milk and caramel topping in a blender until foamy and thick, about 3 to 4 minutes. Divide milkshake evenly among prepared glasses.
Top each with 1/2 cup whipped cream. Sprinkle crumbled chocolate wafer cookies and chopped honey-roasted peanuts evenly over top of each milkshake, and serve immediately.