Preheat the oven to 400F. To a lined baking sheet, add the bacon. Bake for 15 minutes. Remove from the oven, flip the bacon over, and bake for another 5-10 minutes or until the bacon is looking almost done and crispy, but could go for another 8 minutes (we want the bacon very crispy in the end). Time will vary based on how thick or thin your bacon is, so keep an eye on it.
Scooch the bacon over to make space for the dates. Add the date pieces and gently toss in the bacon fat. Bake for another 6-8 minutes or until the dates are starting to caramelize. You can remove the bacon if it looks done before the dates are done.
Use a slotted spatula to transfer the bacon and dates to a paper towel lined plate to soak up the excess fat. Once they have both cooled off enough to handle, roughly chop the bacon and then toss with the dates.
Meanwhile, to a large bowl add all of the dressing ingredients and whisk until smooth. Add the herbs, radish, snap pea and/or fennel, and avocado. Use your hands to toss gently to coat.
Transfer to a serving platter or large shallow bowl. Top with the boiled eggs, bacon and date crumble, goat cheese, black pepper, and a generous drizzle of olive oil, if you’d like.