Tomato Basil Soup and Grilled Cheese with Jam

Nothing quite hits the spot on a winter evening like a big bowl of tomato soup and grilled cheese. But who am I kidding, this is quintessential comfort food for anytime of year! You can bet we always have the pantry stocked with a can of tomatoes just for the occasion and are definitely guilty of whipping this together at least once a month. Not only is it incredibly fast to make but it knocks any of those canned tomato soups out of the park! And let’s not forget that perfect dunking accompaniment…grilled cheese. Now this is where you can have some fun. If you’ve never tried it before, jams and jellies are surprisingly wonderful paired with melted cheese, as is sliced fruit. Our favorite combo so far? That would be the fig jam and sliced pears, but peach jelly and apple slices are a close second. Not into the fruit? Tomato and basil is always delicious or spice it up with some sambal and banana peppers. You really can’t go wrong.

Tomato Basil Soup and Grilled Cheese with Jam
Serves 2 generously

For the Soup:

1 TBSP unsalted butter
2 shallots, coarsely chopped
1-2 garlic cloves, minced
3⁄4 tsp sugar
3 TBSP red wine
 28 oz can whole plum tomatoes
1 c. water
5 banana pepper rings from the jar, plus 1 tsp of the juice
1⁄4 c. basil leaves, packed, plus extra for garnish
1⁄4 tsp salt and pepper
2 TBSP heavy cream

For the Grilled Cheese:

4 slices of bread (we like Pepperidge Farm’s Hearty White)
block of sharp cheddar cheese
fig jam
1 bosc pear, thinly sliced
2 TBSP unsalted butter, divided

  • Melt butter in a medium-sized sauce pan over medium heat. Add the shallots and sauté for 2 minutes. Add garlic and sugar followed shortly thereafter by the red wine. Continue cooking another minute then add the tomatoes, water, banana peppers, basil, salt and pepper and bring to a boil.
  • Once at a boil, turn of the heat and carefully pour soup into a blender. Puree about 10 seconds then return to the sauce pan. Over low heat, add heavy cream and stir until blended. Serve with shredded basil on top.
  • Meanwhile, slice up your cheese and cover one slice of bread with it for each sandwich. Layer the pear slices on the cheese layer and spread a layer of fig jam on the other bread slice.
  • In a nonstick skillet, melt 1 TBSP butter over medium heat and add both sandwiches. Cook until bread is nicely browned, then add second TBSP of butter and flip, making sure the butter adequately coats the bread. Once browned, remove from pan, slice and you’re ready for dunking.

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