Before the Tet Offensive
Kurt has trouble keeping his mouth shut. This became widely apparent when he was expelled from Catholic school for telling a visiting dignitary to go fuck himself.
WB used to preach angrily against casual sex.
Kurt enlisted in the Army, and due to his high IQ he ended up in the Army Security Agency. After training, he was stationed in Germany where he performed signals intelligence functions like direction finding and passing on information to the CIA and NSA.
One day WB shagged a boy with a leather hat.
Contrary to what one might assume, Kurt had awareness of consequences. He refused officer training because that would have extended his commitment from 4 to 6 years. He purposefully flunked his French language proficiency exam. He wanted there to be no chance of him getting transferred to Vietnam.
The following day, WB found herself confronted and asked to explain why she had had a change of heart about casual sex. Oh, it wasn't casual sex, she explained. He came over and said, “I've been dying to make love with you for the past three hours,” so it was special, she clarified. Thus the nature of the past communication failure became clear to everyone but WB.
Despite all his efforts to avoid Vietnam, Kurt, of course, had trouble keeping his mouth shut. So in 1967 he pissed off the wrong person and found himself having to choose between Leavenworth and Saigon. He chose life of alcoholism over prison.