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Confession: I sometimes choose a recipe based on it’s name/title alone. That’s what led to me add this dessert to the menu of my recent dinner party. I thought it would be a good conversation piece! Turns out, it was also rather yummy.

This recipe comes from the Colonial Williamsburg cookbook and is a version of the trifle-except instead of layering the elements in a giant glass bowl, you do so in individual servings. I thought it was rather elegant and unique.


• ½ cup shortening
• 1 3/4 cup sugar, divided
• 3 whole eggs
• 3 egg yolks
• 2 ¼ cup flour
• 3 teaspoons baking powder
• ½ teaspoon salt
• ¾ cup milk
• 1 teaspoon vanilla
• 1 quart milk
• 1 teaspoon rum flavoring
• ½ cup sherry (cream sherry is best)
• Whipped cream
• Slivered almonds


Preheat oven to 350 degrees. Grease and lightly flour a square baking pan (9x9x2 or 7 ½ x 11 ½ x 2 inches).
Cream shortening and one cup of sugar.

Creamed sugar and shortening

Add 2 whole eggs and beat until lemon-colored and fluffy.

Fluffiness achieved!

Sift flour, baking powder, and ½ teaspoon of salt together and add to the beaten mixture alternately with the milk, beating after each addition.
Add vanilla and combine.
Pour into baking pan and bake for 35-40 minutes or until toothpick stuck into middle of the cake comes out clean. Cool.

Meanwhile, combine milk, ¾ cup sugar, cornstarch, and 1/8 teaspoon of salt. Heat over medium heat, stirring constantly until slightly thickened.

Slightly thickened means it should be about the consistency of canned mushroom soup.

Beat the egg yolks and the remaining whole egg.
Add 1 cup of the hot milk mixture to the beaten eggs. Stir and then pour back into the hot milk mixture.

Egg yolks and the egg with the cup of hot milk mixture

Continue cooking, stirring constantly, but do not boil, until you reach custard consistency.
Add rum flavoring and sherry. Allow to cool. (I set mine in a bowl on the counter for about half an hour, and then refrigerated it until dinner).

Finished custard is now cooling

To serve, cut a square of cake and place on plate or pretty dessert bowl. Pour custard over top, then top with whip cream and almonds. Enjoy!

Finished Tipsy Squire-don’t worry, it won’t actually make you tipsy.