Prep all ingredients per instructions above.
Preheat the oven to 350°F (176°C). Drizzle the oil over the bread cubes. Season with salt and pepper. Toss until evenly coated. Spread in a single layer over the baking sheet and bake until golden brown and crisp (about 10-12 minutes). Then set aside.
In a small bowl, whisk together garlic, dijon, Worcestershire sauce, lemon juice, and red wine vinegar. Slowly drizzle in extra virgin olive oil while whisking constantly. Whisk in parmesan. Season with salt and black pepper to taste.
In a large skillet, melt butter and add the fresh sage leaves. Cook, stirring occasionally, until the butter is browning and the sage is crisp (about 4 minutes). Remove the sage leaves from the butter and set them aside.
In the same skillet, add olive oil, chicken, chopped shallot, chopped garlic, and dried oregano. Cook until the shallots begin to caramelize, which takes about 3 minutes. Reduce the heat to low, add the tomato paste, pumpkin puree, and red pepper flakes, then cook for an additional 4-5 minutes until the mixture thickens. Stir in the vodka and cook for another 2 minutes. Finally, add the heavy cream, butter, and grated parmesan cheese. Season with salt and pepper. Keep the sauce warm over low heat.
While preparing the sauce, bring a large pot of salted water to a boil. Add the tortellini and cook according to package directions until they are al dente. Just before draining, remove 1 cup of the pasta cooking water. Drain the tortellini.
Add the drained tortellini to the vodka sauce, tossing to coat. If needed, thin the sauce with the reserved pasta cooking water in small increments.
Divide the tortellini among two plates and top with crispy sage and additional parmesan.
Prepare the Caesar salad by tossing Romaine lettuce with Caesar salad dressing. Top with croutons and grated Parmesan cheese.
For garlic cheese bread, preheat the oven broiler on low. Spread the butter and garlic onto the bread. Sprinkle it with cheese. Place the bread slices under the broiler for a couple of minutes, until the cheese is melted and bubbly.
For lemon water, combine water with lemon slices in a pitcher. Serve over ice if desired.
Serve the tortellini with Caesar salad, garlic cheese bread, and a refreshing glass of lemon water.