Grilled Cheddar & Tomato Jam Sandwich

From Laura Werlin, the San Francisco-based author of “Grilled Cheese, Please!: 50 Scrumptiously Cheese Recipes.” (Time is for preparing the sandwich alone. Make Tomato Jam early in the morning for ready use.) Some grilled cheese making tips: -- Grate the cheese. It will melt faster and more evenly than sliced cheese. -- Butter the bread, not the pan. Thinly sliced bread and soft, salted butter work best. -- Cook low and slow. Don’t rush. Grill the sandwich slowly over medium heat. It’s done when the bread is crispy and the cheese is fully melted. -- Cover up. Lock in the heat by covering the sandwich while cooking. -- Press, flip, repeat. Use a spatula to press down firmly on the sandwich while cooking. Flip twice (pressing with each flip).

• Ready In: 25 mins
• Serves: 4

Ingredients

• 12  ounces cheddar cheese
• 4  tablespoons butter, at room temperature
• 8  sandwich-size slices  sourdough bread
• 6  tablespoons  tomato jam (see recipe below and cooking instructions #6)

• Tomato Jam

• 6  large  ripe tomatoes, peeled, seeded and coarsely chopped (about 1 1/2 pounds, use Roma tomatoes if it isn't tomato season)
• 1  garlic clove, finely chopped
• 1⁄4 cup red wine vinegar
• 2 1⁄2 tablespoons sugar (see note in how to make jam)
•  salt

Directions

1. Using the very small holes of a box grater or other similar-size grating device, finely grate 6 ounces of the Cheddar. Place the cheese in a small bowl. Add the butter and, using the back of a fork, mash the mixture until the cheese is well incorporated into the butter.
2. Using the large holes of a box grater or other similar-size grating device, grate the remaining cheese.
3. To assemble: Spread the Cheddar-butter mixture on one side of each of the bread slices. Place 4 slices of bread, buttered side down, on your work surface. Spread 1 1/2 tablespoons of jam on each slice. Distribute the cheese, and top with remaining bread slices, buttered side up.
4. Heat a large nonstick skillet over a medium heat for 2 minutes. Put the sandwiches into the pan, cover, and cook for 3 to 4 minutes, until golden brown. Turn the sandwiches, pressing each one firmly with a spatula to flatten slightly. Cover and cook for 2 to 3 minutes, until the undersides are well browned (watch carefully because the cheese on the outside of the bread can darken quickly). Turn the sandwiches once more, press firmly with the spatula again, cook for 1 minute, and remove from the pan. Let cool for 5 minutes. Cut in half and serve.
5. For sandwich maker method: Preheat the sandwich maker. Follow directions for assembly above. Cook according to manufacturer's instructions.
6. TOMATO JAM: If you're making this in the middle of tomato season when tomatoes are at their sweetest, reduce the sugar by 1 to 2 teaspoons.
7. Cooking Directions: Place all the jam ingredients in a medium-size saucepan over medium-low heat. The mixture should bubble ever so slightly but not boil. Cook for about 1 hour, or until the jam has thickened and most of the liquid has evaporated. Let cool. (You can make this up to 1 week in advance. Store in the refrigerator).