Spiced Chocolate Chip Acorn Squash Ice Cream Sandwiches

Spiced Chocolate Chip Acorn Squash Ice Cream Sandwiches
An Open Letter to the Woman Who Birthed Me,

I worry sometimes that I might be the worst daughter in the world. You’ve taken care of me by yourself for most of my life; you’ve ensured I keep close to our family that is far by affording me the opportunity to visit on various occasions; you’ve listened to me harp on about my crushes; you’ve taken care of me when I’ve been sick; you’ve shared probiotics and vitamins and anything you thought might make me feel as healthy as I possibly can; you’ve shared so many of my blog posts on Facebook; you’ve done countless things to love and support me and my decisions. Meanwhile, I am the person who moved back in with you almost 6 months ago and promptly did two things I am not proud of:

1) I stole your denim jacket and it is hidden somewhere with all of my things and I know that I am entirely incapable of ever returning it.

2) I also broke your melon baller using it for scooping ingredients that were not melon (read: avocado, goat cheese, cookie dough). I should have known better, and I am going to go hide with your my denim jacket until it is safe to come out again.
Spiced Chocolate Chip Acorn Squash Ice Cream Sandwiches
While I am able and willing to admit to the horrible things I have done, I also want to come clean and admit that I didn’t just stop at having broken the melon baller. I probably should have, I realize. Apparently, I lack the fortitude it takes to be wholly good or redemptive, so please know that I aim to one day be one of those people who steals denim jackets only to shamefully return them and apologize endlessly. Right now, however, I seem to be the kind of gal who realizes her villainous ways, takes another step to break that same person’s belongings, and then uses said belonging to scoop perfect little dabs of vanilla ice cream onto chocolate-chipped, cake-like cookies laced with autumn spices and homemade acorn squash puree. To make sandwiches, of course.
Spiced Chocolate Chip Acorn Squash Ice Cream Sandwiches
After 26 years, this is who I am. A crook and a sham. Full of probiotics and decked out in a fancy denim jacket, with a roof over my head thanks to your kindness and generosity, and all I can do is boast about this awesome thing I’ve started doing where I make puree out of the season’s bounty of squash varietals and use it to bake up dreamy desserts. I am (kind of not really) sorry.

Signed,
Your Not-Nearly-Apologetic-Enough Spawn

P.S. Dear readers, did I mention they’re textured like cake? Scented with aromatic cinnamon, pumpkin pie spice, and other autumn notes, these cookies and their brown-buttered, chocolaty counterparts beg for the smooth, cool melt of oozy vanilla ice cream. And so, we indulge. Wrap them like compact presents in parchment paper and share with your loved ones. Pro-tip: it might reinforce how much you love them even if you are mildly difficult, selfish, and destructive sometimes.

One Year: Chewy Toffee Cookies
Two Years: Pumpkin Spice Drop Cookies with Marshmallow Icing

Spiced Chocolate Chip Acorn Squash Ice Cream Sandwiches
Makes 12 Sandwiches

Acorn Squash Puree:
Makes about 2 1/2 cups
1 acorn squash, ends trimmed, sliced in half, deseeded

Cookies:
1 1/2 cups all-purpose flour
1 tsp baking soda
1 tsp pumpkin pie spice
1 tsp cinnamon
1/2 tsp ginger
1/4 tsp chinese five spice
1/4 tsp salt
pinch of cayenne
1 cup dark brown sugar
1 tbsp molasses
1/2 cup unsalted butter, browned and cooled to room temp
1 egg
1 tsp vanilla extract
1 cup acorn squash puree
1 cup milk chocolate chips

Assembly:
About 6 cups of high quality vanilla ice cream (my favorites, in order: Ben & Jerry’s, Häagen Dazs, and Talenti)

Puree:
Preheat oven to 400 degrees Fahrenheit. Place squash halves cut-side down on baking sheet and roast for 30-35 minutes, until cooked through with slight give. Let cool completely before scooping flesh out and mashing. For smoothest consistency, use a food processor to blend into a puree. Make ahead and refrigerate for 1-3 hours before using for cookie recipe. (Note: This makes more than is needed for the cookies. As for the rest of the puree, you can add butter, maple syrup, salt, and cinnamon and serve as a side, or anything else your heart desires.)

Cookies:
In a medium bowl, whisk together flour, baking soda, pumpkin pie spice, cinnamon, ginger, chinese five spice, salt, and cayenne. In a large bowl, beat brown sugar, molasses, and brown butter until fluffy, about 2 minutes. Add egg and vanilla and beat for another 2 minutes. Beat in acorn squash puree until combined. Fold in dry ingredients, stirring until just combined. Stir in chocolate chips. Refrigerate for 30 minutes. Meanwhile, preheat oven to 350 degrees Fahrenheit. Spray a baking sheet with non-stick vegetable oil spray. Once the dough is chilled, use a tablespoon to scoop even spoonfuls of cookie dough onto two baking sheets, leaving enough space between cookies for spreading. Bake for 10 minutes, rotating halfway through, until the centers are soft with a slight give and the edges are golden brown. Let stand on baking sheet for 1-2 minutes before moving cookies to rack to cool completely.

Assembly:
Top bottom side of one cookie with about 1/2 cup of vanilla ice cream. Sandwich with another cookie. Wrap in parchment paper and freeze for at least 1 hour, or until ready to serve. Repeat twelve times. Curse my name after finding you’ve eaten six all by yourself.

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