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Preheat oven to 400°F.
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Place the grape tomatoes on a rimmed baking sheet, drizzle on 1-2 tbsp. olive oil, and toss to coat. Place in the preheated oven and allow the tomatoes to roast for 15 minutes. Remove from the oven, let cool, and mash.
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Place a large skillet over medium-high heat, add in 2 tbsp. of olive oil, and let it heat up. Add in the onion, garlic, asparagus, carrot, and leek. Season with 1 tsp. each of salt and black pepper. Sauté for 2-4 minutes or until onion is translucent and garlic is fragrant.
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Pour in the chicken broth and let simmer for 8-10 minutes or until the soup is heated through and the carrots are fork-tender. Stir in the mashed tomatoes and cook for 2 more minutes.
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To serve, ladle 1 ½ - 2 c. of the soup into each soup bowl and garnish each serving with 1 tbsp. fresh chives. Add a couple drops of tabasco sauce, if desired, for added spice.