Make the Caesar dressing by whisking together the mayonnaise, buttermilk, lemon juice, minced garlic, minced anchovy, Worcestershire sauce, Dijon mustard, sea salt, and freshly cracked pepper, to taste, until well combined. Set aside in the refrigerator until ready to use.
Heat a grill pan over medium-high heat.
Toss the asparagus spears with a bit of olive oil then season with sea salt and freshly cracked pepper; toss to coat evenly.
Place into the grill pan and cook, flipping occasionally, for 4-5 minutes, or until crisp-tender and slightly charred. Place on serving plate.
To serve, drizzle the top of the asparagus with some of the Caesar dressing then top with homemade croutons, freshly shaved parmesan, and lots of freshly cracked pepper, to taste. Serve immediately. Enjoy.