I’m assuming that most of you know how to make a grilled cheese, and so this is less of a recipe than an ingredient suggestion. Many of you share my love of kale (greatest food in the world? perhaps). Butternut squash is up there as well, and I have always loved grilled cheese in just about any form imaginable. So, really, this is a winning combination, and I stumbled on it kind of by accident. It may be the height of my sandwich-making achievements thus far.
I first stuck some kale in a grilled cheese a few weeks ago, when we had a few lonely leaves of kale in the fridge that had accidentally frozen and needed to be used quickly. It wasn’t until the next time I made a kale grilled cheese, a few days later, that I also added squash. I roasted a butternut squash as a side dish, and only decided to also put the squash in the sandwich at the last minute. If you’re not just spontaneously adding squash to your sandwiches like I did, this is going to take a little (but not too much) advanced planning because you need to cook the squash before making the grilled cheese. I cubed the squash and roasted it with olive oil, a little maple syrup, some chile powder, salt, and pepper.
For cheese, I used cheddar, which tends to be the staple cheese in our house and which I really enjoy in grilled cheese. The sharpness of the cheddar was really nice with the sweet squash and bitter kale. But I could also imagine swiss being nice here, or a combination of cheeses.
You’re going to want to butter the outsides of your bread, lay down your cheese, and let that melt in a pan. When the cheese has mostly melted, it’s time to add the squash to one side (I also sprinkled some pepper flakes on the other). Pile the kale on top of the squash — I’ve found that about half a leaf of kale is good for one sandwich. You want to squeeze in as much as you can because it will cook down, and it also helps to make sure that your kale is torn into manageable pieces. Flip the other slice of bread over on top of the pile of kale, press down with a spatula, and flip it a few times until it’s done. Adding the kale just before you press the two halves of the sandwich together gives it enough time to cook so that it’s an appropriate texture for a sandwich but still chewy and kale-like.