Pour boiling water over dates and let cool, about 1 hour.
Preheat oven to 350°
Butter 9-10 spring form pan. Line bottom with parchment paper and butter paper.
Using electric mixer, beat butter and sugar in large bowl to blend. Add maple syrup and mix well.
Add 2 eggs, 1 at a time, beating well after each addition. Add half of flour and beat to blend. Add remaining 2 eggs, 1 at a time, beating to blend after each addition. Add remaining flour and beat until blended.
Combine instant coffee and baking soda in small bowl. Pour into date mixture, stirring to dissolve coffee granules. This will foam slightly. Once granules are dissolved, pour date mixture into batter and beat to blend. Pour batter into prepared pan. Place on rimmed baking sheet and bake until tester inserted into center comes out clean. 50-60 minutes.
Cool pudding until just warm. Un-mold, sprinkle with powdered sugar.
To Make the Caramel Sauce
Bring cream, brown sugar, butter and maple syrup to boil in heavy medium saucepan over medium-high heat, stirring frequently. Reduce heat to medium-low and simmer sauce until reduced to 1 3/4 cups, stirring occasionally, about 15 minutes. (Can be prepared 1 day ahead. Cover and refrigerate. Before using, re-warm over medium-low heat, stirring frequently.)
To Serve
Gently combine the Irish Whiskey with the whipped cream if using.
Cut the sticky toffee pudding into wedges and serve with Caramel Sauce and Whipped Cream.
Notes
Chopping Dates?Can be a royal pain...but I've found that adding some sugar to the mix helps a lot. Whether in your processor or if using a knife; sprinkle them with a bit of sugar and it helps to keep things from sticking and making this part of the job one you hate!