Heat 1 tsp oil in large skillet over medium heat. Add squash in a single layer and brown (about 2 mins). Flip squash to brown other side and sprinkle herbs. (To reduce fat, roast the squash) Cook another 2 mins until browned.
Remove squash, add a tsp oil and place kale, garlic and pepper in pan. Toss until the kale is coated with oil, reduce heat to low.
Add wine and water, toss, cover and cook for 5 mins or more to desired consistency. Remove kale, turn heat to medium.
Add bread, brown for about a min. Flip bread. Turn heat off, but leave the pan on the burner.
Place a layer of squash on the bread, ¼ of the kale to each and a tbsp of cheese.