To prepare pudding, combine 2/3 cup sugar and eggs in a large bowl, stirring with a whisk.
Heat 2 2/3 cups milk, vanilla, and cinnamon in a medium, heavy saucepan over medium heat to 180 or until tiny bubbles form around the edge (do not boil). Gradually add hot milk mixture to egg mixture, stirring constantly with a whisk. Return milk mixture to pan; cook over low heat 6 minutes or until mixture coats the back of a spoon, stirring constantly with a whisk.
Remove from heat.
Combine bread, dates, and raisins in a large bowl.
Pour milk mixture over bread mixture; toss well to coat. Spoon bread mixture into an 8-inch square baking dish coated with cooking spray. Cover and refrigerate 4 hours or up to overnight.
Preheat oven to 35
Place baking dish in a 13 x 9-inch baking pan; add hot water to pan to a depth of 1 inch.
Bake, covered, at 350 for 20 minutes. Uncover and bake an additional 40 minutes or until a knife inserted in center comes out clean.
To prepare sauce, combine 2 tablespoons sugar and egg yolks in a medium bowl, stirring with a whisk.
Heat 1/2 cup milk in a small, heavy saucepan over medium heat to 180 or until tiny bubbles form around the edge (do not boil). Gradually add hot milk to egg yolk mixture, stirring constantly with a whisk.
Place milk mixture in pan; cook over low heat 6 minutes or until mixture coats the back of a spoon, stirring constantly with a whisk.
Remove from heat; stir in liqueur.
Place pan in a large ice-filled bowl for 5 minutes or until sauce cools to room temperature, stirring constantly.
