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Dining Tip: Grilled Cheese and Spicy Tomato Soup

A simple, tasty and warming meal to pair with Pinot

Jennifer Fiedler
Posted: January 9, 2012

Note: This recipe originally appeared in 8 & 20, our wine and food matchmaking series.

• 2 shallots, thinly sliced
• 1 cup wine (whatever you're drinking will work best)
• 2 28-ounce cans whole tomatoes, preferably San Marzano
• 4 cups chicken stock
• 1 tablespoon crushed red pepper flakes
• 1 loaf multigrain or whole wheat bread cut into at least eight 1/2-inch slices
• 8 tablespoons unsalted butter (1 stick), softened
• 3/4 pound sharp cheddar cheese, grated

1. In a large saucepan, heat 2 tablespoons of cooking oil over medium-high heat. Add the shallots and a pinch of salt; cook until the shallots are soft and slightly caramelized. Add the wine and continue cooking until the wine has reduced by half, then add the tomatoes, chicken stock and pepper flakes and raise the heat to high. When the soup begins to boil, turn the heat down to a simmer, and let the soup continue to cook while you prepare the sandwiches.

2. Butter one side of each bread slice. Assemble the sandwiches with the buttered sides of the bread out and a 1/4-inch layer of grated cheese on the inside. In a large skillet, melt one tablespoon of butter over medium heat. Place the sandwiches in the skillet (two at a time if there's room) and cook until the bread is nicely browned, about 3 minutes a side. While the sandwiches are cooking, press them down using a spatula to get an even grilling. If the bread is getting too brown before the cheese melts, heat the oven to 350° F, and let the sandwiches hang out in the oven until the cheese has melted.

3. Give the tomatoes in the soup a rough mashing with a spoon if they haven't broken up already, check the seasoning, then divide into bowls and serve. Serves 4.


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