Preheat the oven to 350F. Grease a 9x9” baking pan with butter, then line with parchment paper. Set aside.
Start by soaking the dates. In a measuring cup or medium bowl, combine the chopped dates and melted butter. Pour the boiling water on top and stir. Let sit for 10 minutes, or until cool and the dates have softened.
While the dates are soaking, prepare the dry ingredient mixture. In a medium bowl, whisk together the flour, cocoa powder, baking soda, baking powder, salt, and instant espresso powder. Set aside.
Once the dates have softened, pour the mixture into a blender or use an immersion blender to blend until a paste forms.
In a separate large bowl, combine the date paste mixture, both sugars, buttermilk, Greek yogurt (or sour cream), eggs, and vanilla. Whisk until well combined.
Add the dry ingredients to the wet, and use a wooden spoon or spatula to mix until just combined. Scoop or pour the batter into the prepared pan, and spread into an even layer.
Bake at 350F for 48-53 minutes, or until a toothpick inserted into the middle comes out clean or with moist crumbs.
Remove from the oven and allow to cool for 10-15 minutes, or while you prepare the espresso sticky toffee sauce.
In a medium pot or pan over medium heat, add the brown sugar and butter. Bring the mixture to a simmer over medium heat, and allow to simmer for 5-7 minutes, stirring occasionally.
Reduce the heat to low and whisk in the heavy cream. Allow to simmer for another 1-2 minutes.
Then, remove from the heat and whisk in the instant espresso powder, salt and vanilla. Set aside.
Once the chocolate cake is slightly cooled, use a skewer or fork to poke holes all over the surface of the cake. Then, pour ¾ of the espresso toffee sauce all over the top.
Once ready to serve, divide the chocolate espresso sticky toffee pudding into 9 or 16 squares.
Serve warm with a scoop of vanilla ice cream, an extra drizzle of the espresso toffee sauce, and a sprinkle of flaky sea salt if desired.
