Preheat oven to 400°F.
Slice bread slightly on an angle, set aside for bruschetta.
Tomato Jam: in a large sauce pan over medium heat, add olive oil, cherry tomatoes, salt,onion and 1 Tbsp. oregano. As tomatoes cook, break them up with the back of a spoon to release the juices. Cook until mixture has reduced and texture is thickened, remove from heat.
After mixture has cooled slightly, run it through a food mill to remove tomato skins, be sure to press out all liquid. Pour mixture from food mill into a saucepan and add date spread or jam.
Bring to boil and then reduce heat to medium, reduce until texture is thick and large bubbles start to form. Transfer to a bowl and put in cooler until cold and set, about 1 hour.
Caramelized onions: place onions in sauce pan over medium heat with olive oil and salt. When they start to brown and soften, reduce heat and stir in vinegar. Cook until onions are soft and browned.
Bruschetta: brush each slice of bread with olive oil and toast in oven for 2-3 minutes, until browned. After it has cooled slightly, rub cut side of garlic clove into the top of the toast.
Top with tomato jam, sliced ricotta salata, caramelized red onions, and oregano leaves.