Chill your glasses: Pop serving glasses in the freezer for 10 minutes. Cold glasses keep the shake thick longer.
Prep the cookies: Break the cookies into chunks with your hands.
Leave a few larger pieces if you want crunchy bits in every sip.
Add to blender: Add ice cream, 1/3 cup milk, chocolate syrup, vanilla extract, and a pinch of salt to the blender.
Top with cookies: Add 6–8 cookie chunks on top. Reserve any extras for garnish.
Blend briefly: Pulse 3–5 times, then blend on low just until mostly smooth. Stop as soon as it looks thick and pourable.
Over-blending melts it.
Adjust thickness: If it’s too thick to pour, add milk 1 tablespoon at a time. If it’s too thin, blend in an extra scoop of ice cream or a few more cookies.
Serve: Pour into chilled glasses. Top with whipped cream, a drizzle of chocolate syrup, and crushed cookies or chocolate shavings.
Enjoy right away: Milk shakes are best fresh, while cold and thick.