In Baltimore, John and Andre meet Bruce, a homeless, one-legged former construction worker, who is struggling to keep his life together, begging for change while hobbling around on a very outdated prosthetic limb. The crew attempts to find a prosthetic company willing to donate a $22,000 prosthetic leg. The Bruce story is intertwined with the story of Kim, from Stamford, Connecticut, a young woman with a comfortable job who wants to do more with her life. The crew searches for a non-profit agency interested in hiring Kim.

Reportedly filmed on a "dress rehearsal" day at the very beginning of production, this episode concerns Cleveland and Gary, an asthmatic builder in need of a new cell phone, and a recovering heroin addict, respectively. Inspired by John and Andre's life philosophy, Cleveland quits his job as the cameras roll, and shortly thereafter has an asthma attack on the side of the road. In the meantime, and very much to John's chagrin, Andre has added heroin addict Gary to the mix, packing the four men into Jackie's cab like sardines. As though all this were not enough, it turns out Cleveland and Gary have more in common than they would have guessed.

In Baltimore, John and Andre meet Amber, a former stripper, and her rodentine boyfriend. Amber wants to become a model, and the crew sets about finding a model agency that will meet with her, although her domineering boyfriend seems visibly opposed to the idea. The episode is intertwined with the story of Jan, a Huntington, West Virginia native, who plays his mostly-broken keyboard on the street for money. The crew sets about finding him a place that will repair his keyboard. Though the keyboard was beyond repair, the gentlemen who promised to repair it gave him a new keyboard instead.

In Woonsocket, Rhode Island, John and Andre encounter Mark, a homeless alcoholic living in a tent in the woods. Mark has attempted to go to detox in the past, but a $250 deductible is standing in the way. As darkness falls, the crew is faced with the choice of breaking one of its cardinal rules, by spending its own money, a decision which splits the group in two, and causes the mild-mannered Molly to use an unexpected swear word. Additionally, the crew meets Mark's tentmate Normand, who seems to be in even worse shape than Mark, and who at the time is completely inebriated. John and Andre worry that Normand may seduce Mark back to the woods. Both John and Andre are concerned about whether Mark will indeed go through with detox, although the ordinarily bubbly Andre is especially pessimistic.

While traveling through New Rochelle, New York, the team meets Stephen, an out-of-work chef, about to be evicted from his home. He is especially concerned about how this will impact his daughter, Asia, who he dotes on. The RV crew scrambles to line up interviews with restaurants in the area, although it begins to look as though he will have no choice but to leave his apartment.

Easily the strangest episode of the season, John and Andre meet John, a conniving old man with breathing problems (who, despite this, continues to smoke constantly), who needs a stronger air conditioner. Along the way, they meet Erin, who, like Amber, wants to be a model. The RV team is flabbergasted at the difficulty of keeping New Yorkers on the phone long enough to make their pitch, and Erin appears as though she might flake out and not show up at all the next morning. The episode is particularly noteworthy for its inclusion of eccentric modeling guru Candy Ford.

This episode concerns Tom and Mary, a Baltimore couple struggling to open a bar, and Kevin, a young man from Providence, Rhode Island with a stuttering problem, who wants to go on his first date. Kevin is ready to go, but his parents are not so excited.

John and Andre meet Kim, a single mother in Louisville, Kentucky, who is struggling to make ends meet and needs to fix her dryer. The episode is intertwined with the story of Mike, who is dangerously overweight and looking to get his life back on track.

This episode involves Terrence, an Akron, Ohio native with a fantastic singing voice who was fleeced by a shady producer. We also meet West Virginia native and spousal abuse survivor Robyn, who is looking to get a criminal law degree, but has so far not made it through the application process. The team attempts to get them moving in the right direction.

While watching an episode of Dog The Bounty Hunter, a man named Timothy saw a commercial for Random 1, and recognized a man he had not talked to in thirteen years—Normand, from Episode 4, his estranged father. He contacted the Random 1 team, and with his help they, along with a now-sober Mark, returned to Woonsocket, Rhode Island to search for Normand.