Heat a large skillet over medium heat and add the olive oil. Once it's hot, add the ground beef, garlic cloves, salt, and pepper. Break the mixture apart with a spoon and cook until browned, stirring over and breaking the pieces into crumbles, for about 6 to 8 minutes.
Turn off the heat and sprinkle about 2 ounces of the cheddar over the beef so it slightly melts. You can serve this salad with the beef hot or room temp - so if necessary, you can make this a bit ahead of time!
Place the butter lettuce on a cutting board and run your knife through it to chop it into pieces. Ideally we want everything in uniform pieces so each bite is perfect. Chop up the lettuce, then throw it in a bowl with a pinch of salt and pepper. Toss it well.
Add the tomatoes next, the dill pickles, and the diced onion. Add the remaining shredded cheese. Toss the salad well, drizzle on the dressing and serve!
In a bowl, whisk together the pickles, pickle juice, shallot, garlic, mustard, and honey. Add a pinch of salt and pepper and whisk until the mixture comes together.
While whisking, stream in the olive oil until the dressing emulsifies. This stays great in the fridge for a few days!