Peel and devein shrimp; reserve 3 cups of shells. Boil squash for 20 to 30 minutes or until fork goes in easily. Halve, scoop out and discard seeds; reserve squash in warm oven. Drain tomatoes and reserve liquid; chop the tomatoes. Boil shrimp shells, water and liquid from the tomatoes for 15 minutes; strain and return liquid to pan. Add pepper, garlic and olive oil. Reduce on medium heat for 8 minutes; add tomatoes, kalamatas, capers, oregano and parsley. Bring to a boil. Donate a splash of your wine to the mix. Toss in a dozen shrimp and cook until pink, and tails curl. Add 12 more, then 12 more, fishing out the shrimp as soon as they’re done.
When liquid is reduced to sauce consistency, remove from heat, place a cup of spaghetti squash on each plate, ladle sauce over top and garnish with 9 shrimp per plate; sprinkle with Romano cheese. Pour glasses of wine all around, and appreciate the intense fragrance and hearty flavor of this Pensacola rendition of a traditional Italian dish.