Heat a broiler to high. Place the tomatoes on a sheet pan and broil until the skin is charred and peeling, about 10 minutes. Flip and char the other sides until the tomatoes are soft and begin to release some of their moisture, about 5-7 minutes, depending on your broiler.
*You can also char the tomatoes on the grill, just place them directly on the grate, and flip and rotate them as needed.
When the whole tomatoes are cool enough to handle, transfer them to a board and coarsely chop. Transfer the tomatoes with their juices to a medium bowl. Add the red wine vinegar, red chili flakes, and salt and pepper. Add a generous glug of olive oil and stir. Taste and adjust the vinegar, salt, pepper and olive oil as needed.
Serve wherever, whenever!