In the fall of 1964 LIFE photographer Bill Eppridge spent a semester on campus at Yale, following a first-year student as he faced the considerable challenges of college life.

Freshman year can be tough, especially for those living away from home for the first time. The transition was particularly daunting for Eppridge’s subject, a young man named Timothy Thompson. He came to Yale from Ashland, Oregon, which back then had a population of 9,100. Yale’s admission file summed up Thompson as “A rough country boy with lots of tools and desire.”

Thompson had graduated No. 2 in his high school class of 176 and had been president of the honor society. But Yale was thick with honor students, many of whom had come from fancier backgrounds. While working to fit in socially, Thompson, who had been known as a “brain” in high school, also struggled academically for the first time in his life.

Here’s how LIFE described Thompson’ grade shock in its story titled “The Freshman Blues.”

Reality came crashing down on Tim when he sat in his counselor’s room and got his midterm grades. He almost failed chemistry and math, managed an overall average of 72, well below the class figure of 78. The pain deep on his face, he explained he did not know how to study for tests….”When I think about not making it at Yale,” Tim says, “I know I would be so ashamed. I guess that’s what makes me so scared.”

Fear of failure was not the only pressure Thompson faced. He also struggled to fit in to the Ivy League world. Thompson had been raised in a religious household and was on scholarship, so he needed to find his footing at a campus where many classmates came from a more moneyed background and had different kinds of social experiences.

Eppridge’s photographs document the highs and lows of Thompson’s first months at school, whether he is enjoying games of touch football, buying new clothes in an attempt to raise his sartorial game, or giving major side-eye to a guy chugging from a wineskin. LIFE observed that Thompson, despite all the pressures swirling, had something very important going for him: he seemed to be secure in his identity. “I want to be myself,” he said. “I don’t want to be classified as a sophisticate, a playboy, a screwball, or anything.”

Thompson did make it through Yale, graduating with his class in 1968. From there he spent three years with U.S. Army intelligence, including two years of service in Vietnam. In 1979 he earned an MBA from another Ivy League school, Penn, and built a career as an investment advisor, making his home in Scarsdale, N.Y., before dying of lung cancer at the age of 58.

Thompson’s Yale experiences stayed close to his heart. His obituary included a request that donations be made to either a cancer hospital or to the Yale Alumni Fund.

Yale freshman Timothy Thompson (second row, second from left) at welcoming ceremony for the freshmen, 1964. Back then Yale was all-male, and the school only began to admit women in 1969.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshmen, 1964.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson, a scholarship student from a small town, needed to wash and iron his own clothes; when he returned from a dime store with purchases that included a dust mop, a more well-off dorm mate asked, “What’s that?”

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson, 1964.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson (right), and roommate Richard Loomis shook out a second-hand rug they bought for their dorm room; Thomspon, a scholarship student from a small town, sweated the rug’s $13 cost.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson, 1964.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson studying, 1964.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson (background, right), who was raised by a Baptist family that did not drink, looked askance as a fellow student took a swig a wine skin at a football game, 1964.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson at a football game, 1964.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson arrived at school with a suit and two sports jackets but soon found that he needed to add to his wardrobe to keep up with his classmates, 1964.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson arrived at school with a suit and two sports jackets but soon found that he needed to add to his wardrobe to keep up with his classmates, 1964.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson, 1964.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson, 1964.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson, who had been a varsity athlete the small Oregon town where he grew up, only had time for pickup games at Yale, 1964.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson, who had been a varsity athlete the small Oregon town where he grew up, only had time for pickup games at Yale, 1964.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson, who had been a varsity athlete the small Oregon town where he grew up, only had time for pickup games at Yale, 1964.

Bill Eppridge/Life Picture Collection/Shutterstock

Yale freshman Timothy Thompson graduated second in his class in his small-town Oregon high school but averaged only a 72 in his first semester in New Haven, 1964.

Bill Eppridge/Life Picture Collection/Shutterstock

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