Wash and dry the fresh produce. Cut off and discard the stem of the pepper(s). Quarter lengthwise; remove the ribs and seeds, then thinly slice crosswise. Thinly slice the gouda and cheddar. Roughly chop the lettuce. Peel the orange(s) and separate the segments.

In a medium nonstick pan (or large for 4 servings), heat a drizzle of olive oil on medium-high until hot. Add the sliced pepper(s); season with salt and pepper. Cook, stirring occasionally, 3 to 4 minutes, or until slightly softened. Add the vinegar (carefully, as the liquid may splatter); season with salt and pepper. Cook, stirring frequently, 30 seconds to 1 minute, or until coated. Turn off the heat.

Assemble the sandwiches using the bread, fig spread, cooked pepper(s), and sliced gouda and cheddar; season with salt and pepper.

Rinse and wipe out the pan. In the same pan, heat a drizzle of olive oil on medium until hot. Working in batches if necessary, add the sandwiches; loosely cover the pan with foil. Cook 2 to 4 minutes per side, or until lightly browned and the cheese is melted (if the pan seems dry, add a drizzle of olive oil before flipping). Transfer to a cutting board and immediately season with salt. Carefully halve the cooked sandwiches on an angle.

In a large bowl, combine the chopped lettuce, orange pieces, and enough of the garlic dressing to coat; toss to coat. Taste, then season with salt and pepper if desired. Serve the cooked sandwiches with the salad on the side. Enjoy!