To kick off chapter 5, Montgomery details the struggles of her scuba certification. She notes that her joy of being underwater is detrimental because she can’t stop smiling and allowing water into her regulator. She overcomes several challenges (eardrum pressure, trouble with the regulator, becoming certified in the New England cold) in order to make it to her first official dive in Cozumel. Their first dive is a drift dive and Montgomery actualizes her dream. She and her fellow divers come face to face with an octopus in its natural habitat for the first time, rather than in an aquarium.