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While the exact origins of the phrase are unknown, it is commonly believed to have been coined by Americans during World War II. Large numbers of American troops were stationed overseas for many months or years, and as time passed many of their wives or girlfriends decided to begin a relationship with a new man rather than wait for the original one to return.
As letters to servicemen from wives or girlfriends back home would typically contain affectionate language (such as "Dear Johnny", "My dearest John", or simply "Darling"), a serviceman receiving a note beginning with a curt "Dear John" would instantly be aware of the letter's purpose.
"Dear John," the letter began. "I have found someone else whom I think the world of. I think the only way out is for us to get a divorce," it said. They usually began like that, those letters that told of infidelity on the part of the wives of servicemen... The men called them "Dear Johns".
A Dear Jane letter is a contemporary version of a Dear John letter addressed to a female lover.
This term is also used to describe letters written in the context of employment, either to inform an applicant that they had not been selected for a job, why employees had been separated from work, or from an employee to their employer upon the employee quitting.