Preheat your oven to 400 degrees F. Line a rimmed baking sheet with parchment paper.

Spread the cherry tomatoes and whole garlic cloves on the prepared baking sheet. Drizzle with 2 tablespoons of olive oil, sprinkle with dried oregano and black pepper, and toss to coat. Arrange in a single layer so the tomatoes have room to blister.

Roast for 22 to 25 minutes, until the tomatoes are wrinkled, bursting, and starting to caramelize at the edges. The garlic should be golden and soft. Pull them from the oven and set aside.

While the tomatoes roast, add the cold feta chunks and softened cream cheese to a food processor. Process for about 1 minute until the mixture starts to look crumbly and combined. With the machine running, drizzle in the remaining 1 tablespoon of olive oil. Scrape down the sides and process another 30 to 60 seconds until the dip is completely smooth and creamy. If it looks grainy, drizzle in a little more olive oil and blend again.

Spread the whipped feta in an even layer on a large plate or in a shallow serving bowl, using the back of a spoon to create a slight well in the center.

Squeeze the roasted garlic cloves out of their skins and scatter them over the feta. Spoon all the roasted tomatoes and any juices from the pan directly over the top.

Scatter torn fresh basil over everything and finish with a light drizzle of olive oil and red pepper flakes if using. Serve warm or at room temperature with bread, pita, or crackers.