I’ve been watching so many '60s period dramas that dressing up to make cookie salad felt like a fun thing to do. And it totally was! I figured since we had so much fun with classic tater tot hotdish, it was also time to make another classically upper Midwestern delicacy, the cookie salad. Cookie salad blows the other upper Midwest sweet salads, like candy bar salad, out of the water. Easily. It’s not like hotdish, where wild rice and tater tot would definitely make for an edge-of-your-seat 7-game neck-and-neck series. It’s truly more like a UND hockey team versus every team in their conference situation, where they are just in an entirely different league and there are fireworks at every game.

A typical cookie salad consists of the following things:

Fudge stripe cookies

Canned Mandarin oranges or sliced bananas

Vanilla instant pudding mix stirred into buttermilk

frozen whip

They all get mixed together into a fluffy puddingy dessert and then topped with crushed cookies or cookies broken in half and stuck on top to look like little tombstones. This is an important distinction. Your family either crushes or breaks and there’s not a whole lot of overlap except for now because Eggmom crushes and look, I break. I just like the aesthetic, ok? Eggmom taught me both though. She also taught me that mini marshmallows and jelly beans are acceptable mix-ins (I love the textural sensation that marshmallows add).

And,

Ok,

Here is where things get a little…different: Eggmom serves this with the main course. And so does everyone else!!!!! I thought I was hearing things when she said she serves it with the ham (!!!!) but as I dug further and further it slowly became clear that this. is. actually. served. with. the. salads. and. not. the. desserts.

This is a next level sweet/savory relationship, right????

If ham and cookie salad can work as a marriage then surely we aren’t all doomed.

I present to you, my audition picture for women laughing alone with salad:

On my journey to a homemade cookie salad, I did the following:

Made homemade fudge stripes! I went with a simple buttery shortbread that’s sweet and crispy and has a hint of almond. And rather than dealing with the mess of getting chocolate on the bottom, like regular fudge stripes, I gave them thicker-than-usual stripes on top.

In place of the pudding + buttermilk combo, I experimented a bit with making homemade buttermilk pudding but found the buttermilk to be just too sour for my tastes. I don’t remember it being this sour when Eggmom made me hers. I wonder if something in the instant pudding packets offsets the sourness of buttermilk. Instead I went with a rich vanilla pastry cream.

And instead of frozen whip I obviously went with a good old fresh whip because duh. I’ve always been a sucker for fresh whip, it is the heavy cream at its best. I’m using Land O Lakes® Heavy Whipping Cream here which has a deliciously pure flavor.

I stuck with the canned mandarins for this but you could definitely go with fresh mandarins as well.

Lastly, here is a pro-tip: make this the day before so the cookies soak in the pudding and take on a cake-like texture. It is so satisfying. I love it forever. And of course the fact that this can be prepped a day (or even two days!) ahead of time makes this a perfect Thanksgiving dessert. I mean salad! Omg.

Classic Cookie Salad

Serves 8

ingredients

For the pudding

3 tb (24g) all-purpose flour

6 tb (75g) sugar

1/4 tsp kosher salt

3 egg yolks

1 1/2 c (360g) Land O Lakes® Heavy Whipping Cream

1 tsp vanilla extract

1/4 tsp almond extract

For the cookies

1 c (130g) all-purpose flour, more for dusting

1/2 c (60g) powdered sugar

1/2 tsp kosher salt

1 tsp vanilla extract

1/2 tsp almond extract

1/2 c (113g) Land O Lakes® European Style Unsalted Butter, cold and cubed

5 oz semi-sweet chocolate chips

For assembly

1 1/2 c (360g) Land O Lakes® Heavy Whipping Cream

1/4 c (30g) powdered sugar

2 (11 oz) cans mandarin orange slices

Sprinkles, optional

Clues

To make the pudding, combine the flour, sugar, and salt in a medium saucepan. Whisk in the egg yolks and then the heavy cream. Heat over medium heat, stirring constantly until it’s thickened and coats the back of a spoon. Add the vanilla and almond extracts, pour into a heat safe bowl, and cover with plastic wrap so that it touches the surface of the pudding. Refrigerate until cooled, about 1 hour or overnight.

To make the cookies, combine the flour, powdered sugar, and salt in a stand mixer fitted with a paddle attachment. With the mixer running on low, add the vanilla and almond extracts and then gradually add the butter. Mix until the mixture comes together into a dough, slowly increasing the speed once you’re confident that doing so won’t result in flour flying everywhere. Divide the dough in half, press into discs, wrap in plastic wrap, and refrigerate for 30 minutes or overnight. (If you’re impatient, fine, skip this step.)

Preheat the oven to 350ºF, and line two baking sheets with parchment paper and set them aside. On a floured surface, roll out the dough to 1/8”-1/4” thick. Cut out 2” circles with a biscuit cutter and then use a big piping tip to cut out 1/2” holes from the center. (Re-roll scraps as needed.) Place them on the baking sheets an inch apart and then bake until they’re jusssst starting to brown around the edges, start checking for doneness at 12 minutes. Let cool on the pans. Meanwhile, melt the chocolate in a double boiler or in a microwave in 30 second increments, stirring after each. Let it cool slightly and then pour it into a piping bag. Snip off the tip and then pipe on 4 thick chocolate stripes. Let the chocolate harden at room temp or in the fridge.

To assemble, first make the whipped cream. In a stand mixer fitted with a whisk attachment, beat the cream and powdered sugar to stiff peaks. In a large bowl, fold together the whipped cream and pudding. Crush the cookies by hand or in a ziplock bag with a rolling pin or other blunt object (reserving 6-8 for the topping) and fold them in. Drain the mandarin slices and fold those in (reserve some of these for the topping too). Top with remaining cookies, mandarin slices, and sprinkles. Refrigerate until you’re ready to serve.

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