Make the tomato jam: In a medium saucepan, combine the cherry tomatoes, brown sugar, apple cider vinegar, ginger, salt, cumin, paprika, and red pepper flakes. Bring to a simmer over medium-high heat, then reduce the heat to low and simmer, stirring occasionally, for 45–60 minutes, or until most of the liquid has evaporated and the mixture has thickened to a jam-like consistency. Remove the pot from the heat and let the jam cool. The jam will keep in an airtight container in the refrigerator for up to 2 days.
2. Step
Make the grilled cheese: Spread ½ tablespoon of butter on one side of each slice of bread. Sprinkle the buttered sides with ¼ teaspoon pepper each.
3. Step
Heat a large nonstick skillet over medium heat. Place one slice of bread, buttered side down, in the skillet. Spread ¼ cup (60 g) tomato jam over the bread, then layer the Cabot Seriously Sharp Cheddar on top and cover with the remaining slice of bread, buttered side out. Cook for 2–3 minutes, until the bottom slice of bread is golden brown, then use a spatula to flip the sandwich and cook for another 3–5 minutes on the other side, until the bread is golden brown and the cheese is completely melted. Remove from the pan and let rest for 1 minute before slicing.