Melt the chocolate: In a small bowl, combine the chocolate chips and olive oil. Microwave for about 30–45 seconds, stirring until the chocolate is smooth and fully melted.
Add the spider legs: Break three pretzel sticks in half to make six legs. Carefully twist an Oreo apart and press the pretzel pieces into the cream filling on one side.
Secure the cookie: Spoon about ½ teaspoon of the melted chocolate over the pretzels to hold them in place, then press the other Oreo half back on top.
Decorate the spider: Dip one side of the cookie into the melted chocolate. Quickly add two candy eyeballs and sprinkle on chocolate sprinkles for that spooky finish.
Chill and set: Place the cookies in the fridge for about 10 minutes, or until the chocolate hardens and your Oreo Spider Cookies are ready to enjoy.