For dressing, using the Funnel, measure oil, milk, dressing mix, mayo, and lemon juice into Cruet. Screw on lid; shake to mix. If making ahead, cover and refrigerate up to 5 days.
For salad, cut romaine into long spears and arrange on a Sheet Pan. Cut tomatoes in half; scatter overtop. Drizzle dressing overtop and finish with cheese and bacon topper.