Five The Real World alumni gather together to travel across the world for a handsome reward. The cast mates were given enough money for nine days and the keys to the winnebago. Rachel and Sean connect instantly and begin to flirt. The cast mates are given their first clue from infamous The Real World: San Francisco alum David "Puck" Rainey. The cast mates are given instructions to drive to Connecticut where they meet two demonologists and are informed that they will have to spend the night in a supposedly haunted mental hospital. During their mission, the boys decide to play a prank on the girls by pretending to be ghosts. Eric upset one of the demonologists because of his immaturity, but he later apologized. It's later revealed that they did, in fact, catch a ghost on camera and have completed their mission. The episode ends with Puck informing the group that they will be going to New Zealand for their next mission.

The cast mates head to New Zealand for their next mission where they receive a clue that they will be going to a sheep farm. Rachel opens up about her accident as things continue to heat up between her and Sean. The cast mates stop to get breakfast and arrive at their mission an hour late. They're immediately put to work: sheep shearing. The girls are assigned to milk cows which they complete and manage to make up for the loss time. The cast mates are paid and are told they won't be getting any money for another twelve days. Sean gets annoyed when the rest of the cast go out to eat. Eric begins to gain the ire of some of his cast mates for his personality. The cast mates are given their next clue and are told to drive outside Wellington to participate in "Fly By Wire", which they complete. The episode ends with the cast reflecting on the relationships they have with each other.

The cast are given their next clue where they're told to write a new theme song for Road Rules. Eric chose to isolate himself from the project because he was afraid it would conflict with his record deal contract. The cast drive to a field to compete against each other in a sport called "zorbing". During the mission, Jon gets hurt, but turns out to be fine. When it comes down to Rachel and Cynthia to compete against each other, Cynthia bows out, allowing Rachel to win $150. Eric gets into a fight with Cynthia, Rachel, and Sean when he wants to stay. Cynthia and Rachel get into an argument over Eric and Cynthia's alleged "connection" in Connecticut. When the cast arrives in Auckland, Eric tries to make amends by suggesting they go horseback riding. The cast have a good time in New Zealand and things begin to look more positive for the group.

The cast arrive into town where they are told that they will be jumping off the side of a building. Cynthia is terrified to jump, but does it anyway for the bragging rights. The cast are given their next clue and are told they will be going to Los Angeles next. They head over to The Real World: Los Angeles alum Beth Stolarczyk's house to rest before receiving their next clue which is working at "Hot Dog on a Stick". Rachel initially refuses to wear the uniform because she finds it embarrassing, but agrees to do it for the good of the team. The breeze through the mission and get paid. Their next clue tells them they will have a cook off. That night at Beth's place, Beth begins making advances at Sean, but he doesn't give in. The men face off against the women in the cook off. The guys cook up insects in their meal, which they serve to the girls and when they reveal the ingredients, Cynthia gets really upset. The episode ends with Cynthia wanting to leave the show.

The morning after, Cynthia decides that she is going to stay. The cast mates meet with actress Mindy Sterling where she teaches them how to perform improvisation. After performing their comedy routine, the cast are instructed to play parodies of their old The Real World cast members, which goes off splendidly. Other actors present in the performance include Jennifer Coolidge and Cheryl Hines. Their next clue has them recording the song they were told to write a while ago. They meet with a recording producer to record the song. Sean initially becomes embarrassed by his lack of singing talent, but manages to pull through and complete the mission. The cast go out to party where Rachel and Sean hook up. Their final clue tells them they will be taken by limo to their handsome reward. Puck arrives on the scene to drop off their handsome reward, which is a paid trip for two to San José, Costa Rica. Sean and Rachel affirm their attraction to each other. The episode ends with the cast reflecting on their adventure together and the full theme song that they wrote together.