Image credit to: Boston Organics (Beth Harris)
Preheat oven to 350. Grease an 8" or 9" round cake pan, line bottom with parchment and lightly grease parchment.
Place dates and baking soda in small bowl. Cover with boiling water and set aside until very soft, about 10 minutes.
Meanwhile, in medium bowl, whisk together flour, cocoa, salt, baking powder and espresso powder.
When dates are nearly done soaking, whisk together brown sugar, whole egg, egg yolk and vanilla in large bowl until sugar is completely dissolved and the mixture has lightened in color, about two minutes. Continue whisking and slowly drizzle in oil, keep whisking until mixture is emulsified, creamy and shiny.
With rubber spatula gently stir flour mixture into egg mixture, when nearly incorporated drain dates and add to batter with chocolate chips. Transfer batter to prepared pan and smooth top.
Bake cake 18-22 minutes, until top feels set and a toothpick inserted in center comes out mostly clean but with a few streaks of chocolate. Place cake in pan on cooling rack for 10 minutes or so, then remove from pan and allow to cool completely.
Serve with whipped cream or frosting of your choice,
Will keep at room temperature for about 4 days if well wrapped.