Mary Kay Letourneau was at the forefront of improper teacher/student relations.
In 1996 at the age of 34, she began having relations with her sixth grade student, Vili Fualaau. She spent seven years in jail because of the incidents, but soon after she was released, returned to Fualaau, and they married in 2005.
After 12 years of marriage, however, the pair filed for separation earlier this month. They have not filed a renup or separation contract, and they have two daughters together who are no longer dependent.