On the fifth season Teen Mom 2 episode that originally aired August 20, 2014, Jenelle filed for divorce from her husband Courtland. Her boyfriend, Nathan, was back home with her after a short stay in jail. While he was gone, Jenelle had a hard time taking care of his destructive dog. Jenelle was pregnant on this episode of the reality TV show with her second son, Kaiser. She and Nathan plan to get married eventually. Nathan is divorced and does not have custody of his daughter. Jenelle's mother, Barbara, has custody of her son, Jace. Jenelle is studying to be a medical assistant.
Being married is not as easy as Kailyn thought it would be. Her husband, Javi, went to Texas to train for his U.S. Air Force job for 30 days. Kailyn remained at their Delaware home to take care of her son, Isaac, and her and Javi's newborn son, Lincoln, which she finds frustrating at times. She has made amends with her estranged mother, Suzi, Isaac's father, Jo, and Jo's girlfriend, Vee.
Chelsea bought a house and received her license to work as an esthetician. Her daughter, Aubrey, started playing t-ball. Chelsea expected Aubrey's father, Adam, to be at Aubrey's first practice session, but he didn't arrive at the softball field until it was over. Adam has not been honest with Chelsea about his legal problems which could affect their custody agreement.
Leah has been feeling better emotionally since she started taking prescription medicine for anxiety. Leah has twin daughters, Aleeah and Ali, from a previous relationship and a daughter, Adalynn, with her husband, Jeremy. Her daughter, Ali, has a rare form of muscular dystrophy. Ali has a temporary wheelchair to help her conserve her energy. Ali's father, Corey, does not want Ali to be wheelchair bound. Leah hopes when Cory sees how the wheelchair helps Ali with her mobility, he will aggressively contact the health insurance company that denied Ali's permanent wheelchair claim.