The Optysmal Times of Teddy Tipper follows the life of a young college student as he uses his undying optimism to get himself into (but mostly out of) a vast array of predicaments.The Optysmal Times of Teddy Tipper follows the life of a young college student as he uses his undying optimism to get himself into (but mostly out of) a vast array of predicaments.The Optysmal Times of Teddy Tipper follows the life of a young college student as he uses his undying optimism to get himself into (but mostly out of) a vast array of predicaments.