Grilled Cheese Sandwiches With Tomato 'Soup' Dip

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Tomato "Soup":

2 pints sweet 100 cherry tomatoes

1/4 cup extra virgin olive oil

1 tablespoon + 1 teaspoon kosher salt

1 1/4 teaspoons freshly ground pepper

1/2 teaspoon hot red pepper flakes

2 tablespoons balsamic vinegar

1 tablespoon sugar, or to taste

1 1/2 cups canola oil

Grilled Cheese:

1 loaf pan de mie (may substitute sliced white bread)

1/2 cup unsalted butter, at room temperature

1 pound extra-sharp white cheddar cheese, sliced thick

1 bunch chives, chopped

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