There Should Have Been Castles

It is the 1950s. Ben Webber is a cocky but disillusioned young man who has spent the last few years of his life waiting for a neighborhood girl--in his eyes, the epitome of lost virtue and beauty - to reach the age of consent so that he can marry her. Ben comes frustrated with his life, though, and leaves his family home in New England to travel to New York in hopes of finding himself. Despite possessing a near-genius IQ, Ben feels no need to strive in academics, instead choosing to toil away in a number of dead-end, low-paying jobs, which he invariably quits or gets fired from after either telling off his boss or getting caught stealing. Down to his last few cigars and without a place to stay, Ben has a chance run-in with Don at a coffee shop; impeccably dressed and exquisitely mannered, Don is nonetheless just as destitute as Ben and facing eviction from his own apartment unless he can find someone to help with the rent. Ben and Don quickly become friends, and Ben moves into Don's apartment, which Ben discovers is actually owned by a trio of airline hostesses who rent the apartment out to Don at a low rate in exchange for providing them anonymous, strings-free sexual favors on their occasional stopovers in town. Ben, a virgin, is initiated into sex by one of the stewardess, and falls in love with her, only to discover shortly thereafter that she is engaged; after one last night, the stewardess relinquishes her third of the apartment and leaves New York, leaving Ben heartbroken and morose.