Prep the asparagus bundles. Group the asparagus into 8 small bundles (2–3 spears each). Wrap each bundle with a slice of bacon, starting near the tips and spiraling down.
Tuck the end under the bundle if you can. Pat dry with a paper towel to help the bacon crisp.
Heat the skillet. Set a large, heavy skillet over medium heat. Add a light drizzle of olive oil if your bacon is very lean.
Place the bacon-wrapped bundles seam-side down in a single layer.
Cook until crisp-tender. Sear for 3–4 minutes per side, turning as needed, until the bacon is browned and the asparagus is just tender. Adjust heat to medium-low if the bacon browns too quickly. Season lightly with pepper.
Make space for the eggs. Nudge the bundles to the edges of the pan.
Crack the eggs into the center, leaving space between them. Sprinkle with a pinch of salt and pepper.
Soft-cook the eggs. Cover the skillet and cook 3–5 minutes, until whites are set and yolks are still runny or jammy. For firmer yolks, give it another minute.
Remove from heat and keep covered while you make the sauce.
Blend the hollandaise. In a blender or with an immersion blender in a tall cup, combine egg yolks, lemon juice, Dijon, cayenne, and a pinch of salt. Blend 5–10 seconds. With the motor running, slowly stream in the warm melted butter until thick and glossy.
Taste and adjust salt and lemon.
Drizzle and garnish. Spoon the hollandaise over the asparagus and around the eggs. Finish with chopped chives or parsley and a pinch of red pepper flakes if you like.
Serve hot. Bring the skillet to the table and serve immediately with crusty bread or roasted potatoes on the side.