Place a rack in the center of the oven and preheat oven to 250 degrees F.
Arrange all the tomatoes (cluster, roma, and cherry) cut sides down, in a baking sheet. Add garlic to pan and roast until tomatoes are slightly shriveled around edges, 1 hour. Cool in pan for 15 minutes when done.

While the tomatoes are baking, heat the chicken/vegetable stock in the microwave for a few minutes or until steam starts to release (mine took 3 minutes). Alternately, you could warm the stock in a saucepan until is starts to simmer. Place 1 tablespoon of olive oil in a 2-quart saucepan on medium heat and sauté the pearl (Israeli) couscous for 5 minutes. Add the stock to the couscous mixture. Lower the heat to medium-low and cook covered for 12 minutes or until the liquid is absorbed. When couscous is cooked, spread on a baking sheet and allow to cool at least 15 minutes.

In a blender, combine the baked Roma tomato, cluster tomato, garlic cloves, 1/4 cup olive oil, lemon zest, lemon juice, water, salt, pepper, and smoked paprika. Blend until smooth.

In a large bowl, combine the cherry tomatoes, pearl couscous, kalamata olives, parsley, basil, and feta cheese. Drizzle in the garlic tomato sauce and stir to combine. Let stand 5 minutes, all the dressing will get absorbed by couscous.