Fill a large bowl with ice and cold water. Bring a large pot of lightly salted water to a boil. Add asparagus and briefly cook uncovered until just beginning to soften, about 1 minute. Drain in a colander and immediately immerse in ice water for several minutes to stop the cooking process. Drain and season with salt and pepper.
Bunch the spears into groups of 5. Place a slice of provolone cheese over the top of each bunch. Wrap a slice of prosciutto, starting at the base of the spears, around the spear-cheese package and secure with a toothpick.
Preheat an outdoor grill for medium heat and lightly oil the grate.
Place each wrapped asparagus bunch on the grill.
Grill until prosciutto is crispy and cheese is melted, about 5 minutes.
