Instructions

for the pudding

Whisk ¼ cup whole milk, 4 large egg yolks, ¼ cup cornstarch, and ½ teaspoon table salt until smooth; set aside
Combine ¾ cup (5¼ ounces) packed dark brown sugar, 2 tablespoons water, and 1 tablespoon molasses in medium saucepan. Cook over medium-high heat, without stirring, until mixture is bubbling all over, 3 to 6 minutes. Reduce heat to medium-low and cook, swirling pan frequently, until sugar darkens in color and mixture is toasty (mixture will register between 275 and 285 degrees), 3 to 7 minutes longer.
Remove saucepan from heat and carefully stir in 2 tablespoons unsalted butter until melted. Carefully pour ¼ cup whole milk into caramel mixture and swirl to incorporate; let bubbling subside. Add 1 cup heavy cream and remaining 1½ cups whole milk and stir to combine (mixture may look broken; this is OK). Return saucepan to medium-high heat and cook, stirring constantly, until mixture comes to boil, 1 to 3 minutes.
Remove milk mixture from heat and, whisking constantly, slowly add milk mixture to yolk mixture to temper. Return milk-yolk mixture to saucepan. Return saucepan to medium heat and cook, whisking constantly, until pudding comes to boil. Continue to boil 30 seconds. Remove from heat and strain through fine-mesh strainer into clean bowl, using spatula as needed to push pudding through.
Whisk 2 teaspoons vanilla extract into strained pudding. Immediately divide pudding between six 6- to 8-ounce glasses or ramekins. Let cool to room temperature, then cover with plastic and refrigerate until cold and set, at least 6 hours.

for the caramel sauce

Meanwhile, combine ⅔ cup (4⅔ ounces) granulated sugar and ¼ cup water in medium saucepan. Cook over medium-high heat, without stirring, until mixture just begins to turn golden, 4 to 7 minutes. Reduce heat to medium-low and cook, swirling pan frequently, until mixture turns amber-colored (mixture will register between 360 and 370 degrees), 3 to 7 minutes longer.
Remove saucepan from heat and carefully stir in 2 tablespoons unsalted butter until melted. Carefully pour ¾ cup heavy cream into caramel mixture and swirl to incorporate; let bubbling subside (mixture may look like it seized; this is OK). Return pan to medium-high heat and bring to boil. Whisk until smooth, about 30 seconds. Remove from heat and stir in ¼ teaspoon salt and transfer to measuring cup or bowl. Let cool to room temperature. (Caramel can be refrigerated for up to 2 weeks. Bring back to room temperature by microwaving in 15 second increments, stirring frequently, until liquid.)
When ready to serve, divide caramel evenly over puddings.

for the dates

Melt 1½ tablespoons unsalted butter in 8-inch skillet over medium heat. Add 6 chopped pitted Medjool dates and pinch table salt. Cook, stirring often, until dates are sizzling and mixture smells fragrant, about 2 minutes. Divide evenly among puddings. Sprinkle with flake sea salt, if using. Serve immediately.