The teens arrive at Hampton Roads Regional Jail for the "Straighten Up" program and are greeted by Captain Ana Kasey, who drives home the seriousness of what they are about to face.
For now, the group is still acting disrespectful and trying to "be slick." This will soon end.
Master Jail Officer Danny Rosario explains to the teens that whether or not to breathe is the only decision they're allowed to make without his ok.
Master Jail Officer Patricia Williams gives the group a look at the underwear that both men and women have to wear in jail.
14-year-old Robert, a self-proclaimed "pyromaniac", is less than impressed with the unsubstantial underclothes.
The group is taken directly to the maximum security wing where inmates immediately crowd in on them.
The officers allow the inmates to get up close to the group for a minute or two, but quickly have to separate them and get the teens out of the room.
The teens have left the maximum security area, but the inmates aren't done with them. Here, Robert gets an idea of what he would be facing if he were actually incarcerated.
Many of the inmates are the same age as members of the "Straighten Up" group. Deshawn leans down to hear the advice this young inmate has to offer.
Next, the group moves to the kitchen where they discover that everyone in the facility must work, and working in the kitchen can be an unpleasant experience.
The inmates call out for the teens to "Bang the trays" to remove the last clumps of food. What's left in the garbage cans after all the banging is a thick, yellowish muck, fortunately not pictured here.
Robert enters a holding cell as Officers Williams and Rosario look on. At first, the teens seem happy to be somewhere quiet and safe. Soon, however, the reality of living in a small, empty room sets in.
Jeffery speaks to Captain Kasey from inside his holding cell. Given some time to reflect, it seems like the idea of going to jail has stopped being funny.
The group sits before a panel of inmates as their parents look on. "Nasty Nard" paces back and forth as he lectures them.
Suddenly, the chairs are pushed aside and the teens brought to their feet as the inmates get up close and personal. Inmate Perry makes an especially big impression.
Nasty Nard gets in Robert's face as his mother, an officer at the prison and an old acquaintance of "Nard's", listens in.
The teens are sent to separate corners to await more personalized visits from the inmates.
Barry, 15, is constantly getting suspended for fighting. Here, he has just turned around to find inmate Perry towering over him. Would Barry like to fight Perry? No, thank you. Is Barry sure about that? Yes. Yes he is.
Inmate Karen is a mother of three who regrets not being able to raise her children. She connects with Jeffery, and helps him to realize how much his own mother depends on him.
Nasty Nard produces a bible and has Robert pledge to be a better person, especially when it comes to respecting his mother.
Get the latest on new episodes, bonus content, exclusive articles and more.