Sticky Toffee Sweet Rolls

1/2 cup granulated sugar, divided
3 1/2 cups all-purpose flour, divided, plus more for flouring
6 tablespoons butter, melted
1 cup milk
1/2 teaspoon salt
1 teaspoon vanilla extract
FOR THE FILLING:
1/2 cup (1 stick) unsalted butter, softened
3/4 cup brown sugar
1/2 teaspoon salt
12 Medjool dates, finely chopped
1/2 cup pecans, chopped
FOR THE GLAZE:
5 tablespoons unsalted butter
1/2 cup brown sugar
1 tablespoon molasses
1/2 teaspoon salt
1/2 cup heavy cream room-temperature
1 cup pecans
PREPARATION
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