Easily add a touch of elegance to your weeknight dinner without spending too much of your time or energy. Stuffed with tender spears of asparagus and oozing with melted Swiss cheese, this isn't your ordinary chicken dinner. Along with a herbaceous tomato sauce and sautéed zucchini, we keep the carbs and calories low, but bring the house when it comes to flavor and presentation.
Trim zucchini and yellow squash ends, halve lengthwise, and cut into ½" slices. Mince garlic. Trim woody ends off asparagus. Coarsely chop half the Swiss cheese and cut remaining slices diagonally. Stem kale and coarsely chop. Rinse chicken breasts and pat dry.
Prepare the Chicken
On a separate cutting board, drizzle tops of chicken breasts with ¼ tsp. olive oil and cover with plastic wrap. Using a meat mallet or small pan, pound chicken breasts to ⅓" thickness. Season both sides with ½ tsp. salt and ¼ tsp. pepper. Sprinkle coarsely chopped Swiss cheese on chicken and divide asparagus spears between chicken so that tops extend just beyond the top of each breast. Roll chicken breast around asparagus stalks snugly, making sure ends overlap slightly.
Cook the Chicken
Heat 2 tsp. olive oil in a medium pan over medium-high heat. Add chicken to hot pan, seam-side down, and sear 3-5 minutes, or until well-browned. Flip and cook 6 more minutes, or until browned. Transfer to baking sheet, seam-side down, and roast 8-10 minutes, or until chicken reaches a minimum internal temperature of 165 degrees. During last 2 minutes of cooking, top chicken with Swiss cheese slices and sprinkle with half the Italian seasoning. Return to oven for final 2 minutes until cheese melts. Wipe pan clean.
Make the Sauce
While chicken cooks, heat 1 tsp. olive oil in a small pot over medium heat. Add half the garlic (reserve remaining for kale) and remaining Italian seasoning to hot pot, and cook 30 seconds, or until aromatic. Add marinara and 3 Tbsp. water. Bring to a simmer and cook 2 minutes, or until slightly thickened. Remove from burner and taste. Season with a pinch of salt and pepper if desired.
Sauté the Zucchini
In pan used to sear chicken, heat 2 tsp. olive oil over medium-high heat. Add zucchini and squash to hot pan and cook 3-4 minutes, or until well-browned. Flip and cook 3 more minutes, or until pieces are tender. Season with ¼ tsp. salt and a pinch of pepper. Transfer to a plate or bowl and keep warm. Return pan to medium heat (no need to wipe clean) and add 1 tsp. olive oil. Add remaining garlic, kale, and 2 Tbsp. water, and cook 2-3 minutes, or until wilted. Season with ½ tsp. salt and a pinch of pepper.
Plate the Dish
Place a serving of kale, zucchini, and squash on a plate. Pool tomato sauce in front and serve chicken on top of sauce.