Throughly rinse produce and pat dry. Stem, seed, and slice red bell pepper into 1/8'' strips. Peel and halve shallot. Slice into thin strips (julienne). Halve grape tomatoes. Rinse steaks, pat dry, and season with a pinch of salt and pepper.

Bring a small pot with 1 1/2 cups water, 1/2 tsp. salt, milk, and butter to a boil. Steadily whisk in polenta and cook until thickened, about 5 minutes. Adding the polenta in a steady stream rather than all at once will prevent it from clumping. Whisk in Parmesan cheese (reserving a pinch for garnish), taste, and season with more salt, if desired. Cover and set aside. Just before plating, whisk in 2 Tbsp. water to loosen polenta. The consistency should be like a smooth porridge.

Heat a medium pan over medium-high heat. Add 2 tsp. olive oil and steaks to hot pan and cook 4-6 minutes on each side, or until a minimum internal temperature of 145 degrees is reached. Transfer steaks to a plate to rest and return pan to medium-high heat. Don't worry if there are browned bits on the bottom of the pan; they're packed with flavor and will be incorporated into the sauce.

Add 1 tsp. olive oil, oregano, pepper, and shallot to pan and cook 4-5 minutes. Add demi-glace and 1/4 cup water to pan and stir to combine. Cook until thickened, about 2 minutes. Add tomatoes, taste, and adjust seasoning with salt and pepper if necessary.

Spoon polenta on plate and flatten into a wide oval. Spoon red pepper demi-glace over polenta. Place a steak on top and garnish with remaining Parmesan cheese and a bit of sauce.