In a large mixing bowl, combine cold whole milk, sweetened condensed milk, and instant vanilla pudding mix. Whisk for 2-3 minutes until well combined and thickened. Refrigerate for at least 10 minutes.

In a separate mixing bowl, beat heavy whipping cream on high speed until firm peaks form, about 3-5 minutes. Refrigerate until needed.

Gently fold the whipped cream into the pudding mixture until smooth, creating an airy texture.

Spread half of the pudding mixture in a 9x13-inch dish evenly.

Slice ripe bananas and layer them over the pudding. Crush Biscoff cookies and sprinkle over the bananas.

Spread the remaining pudding mixture over the banana and cookie layer, smoothing it out evenly.

Garnish with remaining crushed Biscoff cookies and banana slices. Cover and chill for at least 2 hours or preferably overnight.

Serve chilled, scooping portions into bowls and adding extra cookie crumbs or banana slices as desired.