Step 1- Combine the Vegetables
Place the cucumber, tomatoes, onion, and garlic into a large bowl. There's no specific order that matters here just get everything into one bowl together.
Step 2- Add the Dressing
Toss the vegetables with the olive oil, red wine vinegar, Italian seasoning, pepper, salt, and sugar. Mix gently so the tomato slices don't break apart, but make sure everything gets evenly coated.
Step 3- Let It Rest
Let the salad stand at room temperature or in the fridge for about 15 to 30 minutes before stirring and serving. This resting period matters more than you'd think it gives the flavors time to actually meld together instead of just sitting on the surface.
Step 4- Serve Your Way
As the salad sits, liquid naturally accumulates from the tomatoes and cucumber. Serve with a slotted spoon if you want to avoid the extra liquid, or embrace it and use that liquid as a light dressing over greens. Crusty bread also works great for soaking up every last drop.