Start by bringing a pot of salted water to a boil for the orzo. While waiting, trim the asparagus spears into 2-inch pieces, seed and dice the red pepper into 1/2-inch pieces, and chop the fresh cilantro. Once the water boils, add the orzo and cook according to package directions until al dente. Drain and rinse under cold water to stop the cooking process and prevent clumping.
Pat the shrimp dry with paper towels and toss with the jerk seasoning, ensuring each shrimp is evenly coated. Thread the seasoned shrimp onto skewers. Lightly brush the corn with 1 tsp olive oil, coating all sides. I find that removing the husks and silks completely before grilling makes it easier to get those nice char marks that add so much flavor.
Preheat your grill to medium-high heat. Start by grilling the corn for 10-12 minutes, rotating occasionally until it develops a slight char and kernels begin to caramelize. About halfway through the corn's cook time, place the asparagus pieces directly on the grill grates (or on a grill mat if you prefer) and grill for 5-7 minutes, stirring occasionally until they're tender with light char marks. Remove both vegetables to a cutting board as they finish.
Once the vegetables are nearly done, place the shrimp skewers on the hottest part of the grill. Grill for about 1-2 minutes per side until the shrimp turn pink and opaque. Don't overcook them—they'll continue cooking slightly after removal from heat. Transfer the skewers to a plate to cool slightly, then remove the shrimp from the skewers and set aside.
Once cooled enough to handle, cut the corn kernels off the cob using a sharp knife. Chop the grilled asparagus into bite-sized pieces if needed. While prepping vegetables, whisk together the lime juice, water, 2 tbsp olive oil, honey, salt, and black pepper in a small bowl until the honey dissolves and the dressing is well combined. I always make the dressing while vegetables are still warm so the flavors meld beautifully when combined.
In a large bowl, combine the cooled orzo with the corn kernels, chopped asparagus, diced red pepper, and grilled shrimp. Pour the prepared dressing over the salad and toss gently until everything is evenly coated and combined. Garnish with the fresh cilantro and serve at room temperature or chilled. The salad actually tastes better if you let it sit for 10-15 minutes before serving, allowing the flavors to marry together.