Heat the olive oil in a skillet over medium high heat. Add the turkey and cook, breaking up the meat, for 6-8 minutes. Add the garlic, onion, and red bell pepper. Cook for 4-5 minutes until the onion begins to brown.
Add the butternut squash, tomatoes, salt, pepper, Italian seasoning, and red pepper flakes. Cover the skillet and cook until the butternut squash is tender, about 6-8 minutes. Add a touch of water or broth if anything begins to burn. Depending on the size of the butternut squash, it could take a bit longer. For quick-cooking preparation, make sure to cut it into small pieces.