The largest chasm of all at Cranbrook was between the boarders and the “day boys.” Students within the limits of Detroit’s Eight Mile Road had the option to attend the school without boarding. The requirements for enrollment as a day student were generally tougher, leading day boys to consider themselves academically superior. Day boys also had the freedom to leave campus when school let out late in the afternoon. Often those with cars would gas up at nearby service stations, cruise Woodward Avenue and plot “how and where we could get some beer,” said Gregg Dearth, who went by the nickname Daiquiri Dearth. Drugs were generally unheard of, but day boy parties often included someone downing beers or toting bottles of scotch.
Romney began his Cranbrook career as a day boy and quickly adapted to the school’s unofficial code. He was prohibited by his religion from drinking alcohol but excelled at elaborate practical jokes.
During spring break of his senior year, when most of his friends went to Florida for vacation, Romney stayed behind to make movies for an upcoming Cranbrook talent show. For one, he filmed his friends Stu White and Judy Sherman seated at a table to dine on fine china on a Woodward Avenue median as their friend Pike John, now deceased, acted as the waiter. Romney filmed the luncheon until a police officer pulled up. “And that was it,” Sherman said.