Grilled cheese sandwich with tomato-onion jam and arugula

I don’t think you’re ready for this jelly.

“Who doesn’t love a grilled cheese sandwich?”

This was one of my very first lessons in writing.  I was freelancing for a newspaper’s online shopping column, writing about clothes.  I wrote the line, “Who doesn’t love cashmere?” and my editor struck me down.  She said, “Never write this.  Because it causes a subset of readers to go, ‘I don’t like cashmere,’ before mentally checking out and disregarding the rest of the content.”

It was one of those great, unexpected life lessons about not making assumptions.

You may say, “But Stacy!  Really!  Who doesn’t love a grilled cheese sandwich with its salty ooey-gooey-ness?”

 Honestly?  Me.  At least in the beginning.

It’s so funny, but my first contact with nearly all American food was through TV commercials or TV shows.  You may not be aware of this, but the grilled cheese sandwich is put on a bit of pedestal in this country.  Before I ever had the opportunity to try one, it had been built up substantially in my mind.  My first taste of it was Kraft singles sandwiched between two buttered slices of Wonder Bread.  It was a huge let down.

Since then, in my mind, I’m thinking if I’m going to eat a grilled cheese, it’s gotta be a killer grilled cheese.  It has to be good enough for the calories to be worth it.  It has to be so much more than yellow cheese between buttered bread.  It has to be complex and layered and really earn my initial impression of it.

What?  You want more infographics?  Okay!

Here are the players:

Crusty sourdough bread slices:  They have to be substantial and weighty enough to stand up to fatty cheese and provide a textural contrast.  And it has to be “crusty” aka “rustic,” which basically means it needs nice big holes for the cheese to ooooze into and create a new symbiotic cheese-bread species. (I made my own bread.  If you are interested, here’s a recipe and info for a sourdough boule.)

Tomato jam:  Get the recipe here. Tomato and grilled cheese is a great pairing.  The acidity of tomato cuts through the rich bluntness of the cheese.

Arugula:  I like how peppery arugula is and how it adds another dimension that contrasts against the cheese.  I also like a variety of ingredients in my sandwiches, so it’s typically not a tasty sandwich for me if there’s not some sort of vegetable or fruit hiding in there somewhere.

Cheese!:  Any kind that melts like a boss and has a distinctive flavor will do.  I opted for a sharp cheddar.

You’re probably like, “Who needs a recipe for a grilled cheese?”

Dude. This stupid recipe exists.  And of course it’s from Paula Deen.  And of course it has four stars and 40 reviews.  And of course most of them are totally serious.

My recipe for grilled cheese isn’t so much about the list of ingredients as much as it about the method of creating optimum grilled-cheesiness.  Even though making the sandwich is very intuitive, I hope you find some interesting tips in the recipe.

Grilled cheese sandwich with tomato-onion jam and arugula
Recipe type: Sandwich
Cuisine: American
Serves: 1
  • 2 slices from a crusty sourdough bread – don't buy the pre-sliced stuff on the shelves. Buy the kind in the bakery.
  • 3 thin slices (or so) from a block of sharp cheddar cheese – don't use "cheese product"; it should really be cheese. (They try to trick you with their low prices!) ;)
  • 2 spoonfuls of tomato-onion jam.
  • A small handful of arugula (enough to cover out all the cheese so that very little yellow would peek through if you mounded the arugula)
  • 1 tbsp room temperature butter
  • salt, if your cheese isn't salty enough
  1. Texture is a big thing with grilled cheese, so I like to toast both sides of the bread. One side is toasted lightly, to harden the outside surface and get some golden brown edges. The other side is toasted a LOT. We'll start with the lightly toasted sides first (which are the inside-facing sides).
  2. Heat up a cast iron skillet over medium heat. Take half your butter and spread it evenly on one side of the bread slices. Lay them in the skillet. (You don't have to butter the skillet.) Let them toast up and turn a light golden brown, about 1-2 minutes. Don't press down on them too much while they'r toasting because you might create indentations in the slices.
  3. Once lightly toasted, remove slices from the skillet and lay them toasted side up. Turn the heat down to medium-low to low. Spread tomato-onion jam evenly over both slices, stopping a little short from the edge (otherwise your jam might leak out, caramelize, and burn in the skillet when you're cooking the grilled cheese.).
  4. Lay the pieces of cheese evenly across the sandwich, also staying within the edges. You can break up the cheese slices, no problem.
  5. Lay one slice on top of the other, making the sandwich. Then take half of the butter that's left and spread it over the top. (There won't be very much actually, but you don't need too much, thankfully!)
  6. Over low to medium-low heat, placed the sandwich, butter side down on the skillet. Spread the rest of the butter on the other side of the sandwich.
  7. Now begins the slow griddling of the grilled cheese. An issue with a lot of grilled cheeses is that the outside gets all beautiful and toasty but the cheese on the inside is nowhere near fully melted. So, it's important to cook the sandwich over low heat for a longer amount of time, to allow the cheese to melt without burning the bread.
  8. Use a flat spatula to press own the sandwich as it crisps. As the cheese melts, it will flow into the nooks and crannies of the bread and perhaps, bits will even start to come out of the outside of the bread. I love this. I think it's awesome.
  9. After a minute or so, flip the bread and do the same thing to the other side. This isn't a burger where you flip only once. You'll be flipping over and over, trying to get both sides of the cheese to get gooey. I may have gone through about six rounds of flipping when I made my sandwiches.
  10. Periodically, peek in between the bread slices to see how close the cheese is to being full melted. The whole process may take 10 minutes, depending on what kind of cheese you are using.
  11. Once your cheese is fully melted, it's likely the bread is perfectly toasted. But if it's still a bit pale to you, then increase the heat to medium and brown it on both sides to your liking.
  12. The rest happens fast. You have to finish the sandwich and eat it soon after it's done because that's when it's the best! So start moving! You want to pull the sandwich off the skillet and onto a cutting board. Pull the two sides apart. They should be sticking to each other due to the melted cheese, but the crusty bread should withstand your manipulations.
  13. Take your arugula and shove it on a toast slice. Add salt, if your cheese isn't salty enough naturally (but it should be). Top with the other slice. Cut in half. And eat soon after! It will be piping hot and wonderful.
  14. (If you're feeding a lot of people, you can probably make 2-3 sandwiches at a time in a skillet and hold them in a warm oven at 250 degrees F while you work on another round of 2-3 sandwiches. Wait until all the sandwiches are done before you pry them all apart and stuff them with arugula.)

Here are the steps in picture form:

The arugula ends up wilting, as if succumbing to the overbearing molten force of the cheese.  Let this happen.  It is awesome.

YES.  There needs to be another infographic!

(Click for more of my food-related infographics.  For other food-related infographics, visit my Pinterest board.)

  • This is such a great idea! I just made some tomato jam a few weeks ago, and I love arugula on sandwiches. It looks so good!

    • Yay! We’re of like minds! Thanks for the nice comments, Lori.