These cookies don’t taste “healthy,” which makes them the perfect way to avoid breaking any eat-better resolutions. Toasting the oats before adding them to the batter helps maintain their chewy texture, even after baking.
Position racks in the upper and lower thirds of the oven and preheat the oven to 350ºF.
Spread the oats out on a baking sheet and bake until light golden brown, 10 to 12 minutes. Reserve 1/4 cup of the oats for sprinkling and transfer the remaining oats to a medium mixing bowl to cool. Line two baking sheets with parchment paper.
In the bowl of a stand mixer fitted with the paddle attachment, beat the sugar and butter on medium-high speed until lighter in color and slightly fluffy, about 5 minutes, scraping down the sides of the bowl several times. Beat in the egg and vanilla until very fluffy, 2 to 3 minutes more.
In the mixing bowl with the cooled oats, add the flour, cinnamon, baking powder and salt, and mix to combine. Reduce the mixer speed to low, then add the flour mixture to the butter and beat until just combined. Stir in the dates and chocolate by hand.
Drop level tablespoons of the dough on the baking sheets, leaving at least 1-inch of space around each cookie, about 30 cookies total. Sprinkle the cookies with the reserved toasted oats. Bake until the cookies are lightly golden, 12 to 15 minutes. Cool the cookies for 5 minutes on the baking sheets, then transfer to cooling racks to cool completely.