At Cranbrook, Romney helped manage the ice hockey team, and he joined the pep squad. During his senior year, he joined the cross country running team. He belonged to eleven school organizations and school clubs overall, including the Blue Key Club, a booster group that he had started. During his final year there, his academic record improved but fell short of excellence. Romney was involved in several pranks while attending Cranbrook. He has since apologized for them, stating that some of the pranks may have gone too far. In March of his senior year, he began dating Ann Davies; she attended the private Kingswood School, the sister school to Cranbrook. The two became informally engaged around the time of his high school graduation in June 1965.