While on assignment in Oahu, Hawaii, military contractor Brian Gilcrest (Bradley Cooper) reconnects with his old flame Tracy Woodside (Rachel McAdams), now married to an Air Force recruit (John Krasinski). He also spends time with Allison Ng (Emma Stone), a hard-nosed fighter pilot who watches every move that he makes. As they travel throughout the lush terrain, Brian finds himself falling for his feisty guide, while his conversations with Tracy may provide a shocking revelation from their past.