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Step 1
Preheat grill to medium-high. Once hot, clean the grates really well. Then generously oil the grill grates using a long tongs and a folded paper towel soaked with vegetable oil. Close the grill and let it heat back up again.
Step 2
Lightly brush olive oil on cut sides of romaine and tomatoes, and on the corn. Sprinkle with salt and pepper. Place romaine and tomatoes on grill grates, cut sides down. The romaine is the most tender and should cook the fastest, but this will also depend on your own grill and heat. I like a good amount of char to the romaine, as it adds so much nice smoky flavor. Check the tomatoes after they have been grilling for almost two minutes. They will take a little longer to achieve a solid char. As the corn chars, roll the ears to grill all sides. Have a large platter or pan ready, to pull items off as they finish cooking. Once the ears of corn have cooled a bit, cut the kernels from the cob.
Step 3
Arrange grilled romaine and tomatoes on a large rimmed pan or serving platter, overlapping as needed. Sprinkle with grilled corn kernels and bacon pieces. Finish with additional kosher salt and freshly ground black pepper, to taste. Serve with homemade buttermilk ranch dressing.