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In a dry pot over low heat, toast barley until golden. Add vegetable stock and cook until barley is al dente, about 20 to 30 minutes. Set aside.
In a large sauté pan, add olive oil and warm over high heat until oil is almost smoking. Carefully add artichoke hearts, red onion, and fennel. Sauté, stirring constantly until caramelization begins to occur.
Add garlic and red pepper flakes and continue cooking until fragrant. Deglaze pant with white wine.
Remove from heat, add to cooked barley, and stir in pecorino and herbs. Season to taste and set aside to cool to room temperature.
Stuff halved tomatoes with the barley and vegetable mixture and serve at room temperature with a drizzle of olive oil and a sprinkle of minced herbs.