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Heat a generous tablespoon of olive oil in a large skillet over medium-high. Add one smashed clove of garlic, one-third of the chicories, and a good pinch of salt. Cook, undisturbed, for 30 seconds. Then, using tongs, toss the greens quickly for another 10 to 20 seconds; then immediately transfer to a large serving bowl. Note: The chicories don’t have to be uniformly cooked, i.e. it’s OK if some of the greens are more wilted than others. The contrast in textures is nice.
Repeat 2 more times, adding more olive oil, garlic, chicories and salt to the pan in the same manner.
Gently toss chicories with the 2 tablespoons of vinegar. Taste. Add sea salt and more vinegar to taste. Note: I always add more of both until it tastes sharp enough and nicely seasoned. Drizzle with chile oil to taste, or pass it on the side — passing on the side is a good option if anyone is sensitive to heat. Serve immediately or at room temperature.