Slow Run (1968)

After 14 months of living a Bohemian life in New York City, a young Canadian becomes anxious that he is "settling down." To quell this fear, he impulsively buys a plane ticket for an unspecified destination. About a week before his scheduled departure, he wakes up musing as to whether or not he will inform his friends and his landlord. When he suddenly becomes nostalgic about the city, he is angered by his own sentimentality. Nevertheless, he lapses into a reverie in which he recalls his stay in Manhattan--working at an unspecified job, establishing a relationship with a long-haired intellectual, and having brief affairs with a number of women.

Unfortunately the movie Slow Run is not yet available on HBO Max.