Preheat oven to 400°F. Trim woody ends from asparagus spears and place in a shallow bowl. Toss with olive oil, salt, and pepper.
Gather 3-4 asparagus spears and wrap 1 slice of bacon around the middle tightly, forming a snug bundle. Make sure to overlap the bacon so it does not come unwrapped. Place bundle with the loose end down on a rimmed baking sheet. Repeat with remaining asparagus and bacon.
Bake for 25-30 minutes, until asparagus is tender and bacon is cooked.