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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.
In country music, the concept of the "Dear John" letter was the subject of at least two recordings.
The first came in 1953, when then-unknown singers Jean Shepard and Ferlin Husky recorded a composition written by Billy Barton, Fuzzy Owen and Lewis Talley called "A Dear John Letter." Shepard sang the refrain while Husky recited his part -- playing the part of John, a soldier stationed overseas during a conflict, possibly the then-ongoing Korean War. The young soldier excitedly receives and opens a letter from his girlfriend, but then finds heartbreak: She is breaking off the relationship and is marrying John's brother, Don. The song was a No. 1 country and No. 4 pop hit in the late summer of 1953. Several other artists and duet pairings recorded the song in the late 1960s and early 1970s, with the Vietnam War ongoing; meanwhile, Shepard and Husky recorded a follow-up later in 1953 called "Forgive Me, John," which also became a best-selling country hit.
The Taylor Swift song, "Dear John" from her Speak Now album describes an open letter to an ex-boyfriend (possibly the musician John Mayer, according to speculation) because of being manipulated and betrayed by them.
The movie "Dear John" starring Amanda Seyfried and Channing Tatum is another example of this.