Place the crumbled feta, softened cream cheese, Greek yogurt, 2 tablespoons olive oil, lemon zest, lemon juice, grated garlic, and cracked black pepper into a food processor. Process on high speed for 3 to 4 minutes, scraping down the sides of the bowl twice, until the mixture transforms from grainy crumbles into an ultra-silky, fluffy cloud. Taste and adjust seasoning if needed (feta is naturally salty, so no extra salt is needed).

Heat 3 tablespoons extra virgin olive oil in a wide cast iron skillet or saucepan over medium-high heat. Add the whole cherry tomatoes and let them cook undisturbed for 2 to 3 minutes until skins begin to blister and char lightly. Reduce heat to medium, add the sliced garlic, honey, chopped oregano, red pepper flakes, and halved kalamata olives. Sauté gently for 3 to 4 minutes, pressing a few tomatoes with the back of a wooden spoon so they burst and release their sweet, savory juices into the garlic oil.

Spoon the fluffy whipped feta onto a shallow serving platter or wide shallow bowl, using the back of a spoon to create deep, decorative swooshes and swirls. Pour the warm skillet of blistered tomatoes and fragrant garlic herb oil directly over the center of the cold whipped feta. Scatter with toasted pine nuts, extra fresh herbs, and a drizzle of honey if desired. Serve immediately with warm toasted pita wedges or crispy crostini!