For the pudding:

Cup of Yum
1. Preheat oven to 350F (standard) or 320F (convection).
2. Grease 7 pudding molds with butter or grease and line an 8" square cake pan with an overhang.
3. Place dates in a bowl and pour over boiling water. Let it stand for 10 minutes.
4. Mash well with a potato masher (or fork) until it resembles sloppy porridge.
5. Place butter and brown sugar in the bowl of a stand mixer or a large bowl. Beat until combined and smooth.
6. Add eggs, beat until incorporated.
7. Add flour and sprinkle baking powder across the surface. Mix until flour is incorporated.
8. Add the date mixture and mix until well incorporated into the batter.
9. Pour into cake pan, smooth the surface, and bake for 35 minutes or until a skewer inserted into the center comes out clean.

For the wine syrup:

1. While baking, combine wine, sugar, vanilla extract, and cinnamon together in a saucepan to make the toffee sauce. Bring to the boiling point and then simmer over low heat, stirring occasionally, until the sauce reduces, about 30 minutes. Remove from heat and let cool to room temperature.
2. Remove the cake from the oven. While still hot, poke about 40 holes all over the surface using a skewer. Pour over ½ cup pinot noir sauce and leave to soak for 10 minutes.
3. Use the overhang to lift the cake out, cut, serve warm with the remaining warm sauce over the pudding and topped with ice cream or cream.