Jenelle and Kieffer began dating in 2010, and after multiple breakups and reconciliations, they finally parted in the fall of 2012. They had been together for nearly a year when they called it quits. They started out very much in love, but as time went on, their differences became more apparent. Kieffer was 20 years old when he met Jenelle, who was just 16 years old. He was a senior in high school and she was a new student without any friends or family in Charleston, West Virginia. They were both forced to move back home after their breakup because there weren't any jobs available for them in Charleston. This is when Kieffer started working at his father's garage while trying to find another job. During this time, Jenelle got involved with drugs and prostitution to get money for food and rent. She also started dating Kieffer's friend Kyle Johnson, who used to be her teacher. Although Kieffer was aware of this relationship, he didn't care because he loved Jenelle even though she wasn't right about some things. In the spring of 2013, Kieffer found a good job at a gas station in Baltimore, Maryland.