Prepare the Tomatoes: Wash tomatoes and slice each in half horizontally. Scoop out the insides while keeping the skins intact.

Apply the Pesto Sauce: Pour pesto into a squirt bottle and squeeze around the inner rim of each tomato half.

Fill with Cream Cheese: Use a spatula to fill each tomato half with cream cheese, mixing in some pesto.

Add the Black Olive Pupils: Press a sliced black olive into the center of each filled tomato.

Enhance with More Pesto: Squirt a small dot of pesto into the center of each olive pupil.

Plate and Serve: Arrange on a large basil leaf or festive platter and serve immediately.