With over 1 billion views across his social media platforms, 17-year-old Jack says he'll do almost anything for a "like" and is known for posting outlandish pranks, and most recently, "Karen" videos online. But how far is too far? Jack's parents say Jack continues to push the envelope with his rude and disruptive pranks, and as a result, has had close encounters with the police. His family says they fear for Jack's future and hopes Dr. Phil can weigh in before it's too late. Find out what happens when Dr. Phil meets Jack, his family – and even his neighbor – who claims she feels harassed by his online videos.

Michelle's jobless grandson, Conner, 22, does not regularly shower, brush his teeth, shave, clean his room or change his clothes, and has never met his girlfriend of five years in person; his mom says Michelle is being too strict.