Preheat the oven to 375˚F and lightly grease a 12-inch skillet.
Bring a large pot of salted water to a boil. Slice off the top and bottom of each onion, then peel. Make a cut in each onion halfway through the onion (to the center) so there's a slit. Add the whole onions and simmer for about 15 minutes, until the onion is softened.
Remove the onions and let cool until they are easy to handle. Carefully peel off each layer of the onion, and set aside. We discarded the outermost layer. When you get to the center and cannot get a large enough petal to use for filling, set it aside and finely dice it to use in the meat filling.
In a separate large skillet, cook the chopped bacon over medium heat until crispy and browned, then remove with a slotted spoon to a plate lined with paper towel.
In the same skillet, cook the ground beef, breaking it apart until no longer pink and fully cooked through. Remove it from the pan with a slotted spoon and set aside. Discard most of the fat, leaving just about 1 tablespoon in the skillet.
Add in the chopped onion, garlic and tomato paste, cooking for just a minute or two.
Add back in the cooked ground beef, bacon, Worcestershire sauce, ketchup, mustard, smoked paprika, salt, pepper and ¼ cup of beef broth. Cook for 1-2 minutes, stirring until well combined and moist. Remove from heat.
Stir in the breadcrumbs, then let it cool for a few minutes. Stir in the pickles and the cubed cheddar, mixing just until evenly incorporated. You don't want the cheese to fully melt into the ground beef – it will melt into distinct pockets in the oven.
Take an onion petal and scoop about ¼ cup of filling into the center, rolling the onion around to enclose the filling. The larger onion peels can be cut in half.
Place the filled onions seam side down in the prepared skillet, arranging them in one layer. Repeat with all remaining onions/filling. Pour in the remaining ½ cup of beef broth.
Cover with a lid and bake for 20 minutes, then remove the lid and bake for another 20-25 minutes, until the onions are light golden brown on top.
While the onions are cooking, whisk together all ingredients for the dressing. If it's too thick, thin it out with more pickle juice or a splash of water.
Serve the stuffed onions warm with dressing drizzled over the top, sesame seeds and (optional) chopped parsley for some freshness. Enjoy!