In this episode, Jo heads to Boston to help 31 year-old single widowed mother Jillian, who has 2 children Rowan (14), and Kenisha (5 1/2). Rowan has no respect for his mother and calls her every name in the book. He also likes to sneak out late at night and go to his friends house to do drugs. Meanwhile, Kenisha is a sweet, well-behaved little girl who is unaware of what is going on and is feeling left out due to her big brother's behavior. Will Jo's Lose What You Like Chart and Naughty Tent be able to stop this tearaway teen?