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Bring a large pot of salted water to a rolling boil and cook 1 pound cheese tortellini according to the package instructions.
Drain the pasta and rinse with cold water to cool it.
Once cooled, shake off the excess water and toss it with a little olive oil. Set aside.
Prepare the dressing by whisking ½ cup mayonnaise, ½ cup sour cream, ¼ cup milk, and 1 (1-ounce) packet Ranch seasoning mix together in a small bowl.
Add 2-3 cups chopped romaine lettuce, 1 pint halved cherry tomatoes, ½ pound crisply cooked, chopped bacon, and ½ cup thinly sliced shallot to a large bowl and top with the dressing.
Toss until evenly coated. Cover and refrigerate until you are ready to serve.