Wrap each asparagus spear with a half slice of bacon, starting at the bottom and spiraling up to the top, securing with a toothpick if needed.
Heat 2 tablespoons of olive oil in an oven-safe skillet over medium heat, then add the bacon-wrapped asparagus and cook for 3-4 minutes, turning occasionally, until the bacon begins to crisp.
Transfer the skillet to the preheated oven and bake for 8-10 minutes, or until the bacon is fully crispy and the asparagus is tender.
While the asparagus cooks, prepare the fig vinaigrette: In a small bowl or blender, whisk or blend the fig jam, balsamic vinegar, olive oil, Dijon mustard, honey, and a pinch of salt and pepper until smooth, adjusting seasoning to taste.
Remove the asparagus from the oven, discard toothpicks if used, and arrange on a serving plate.
Drizzle the fig vinaigrette over the bacon-wrapped asparagus and serve warm.