While at a 20th century museum, Fry runs over another bending unit, Flexo. When Flexo is hired at Planet Express as extra security for the delivery of the tiara to the Miss Universe Pageant, Fry becomes suspicious of him and keeps watch on him for most of the journey. Tired, he falls asleep while guarding the tiara and when he wakes up he discovers it has been stolen.
Bender gets into trouble with a famous wrestling robot and accidentally knocks him out. Instantly, he is offered to fight in the professional robot wrestling league and Leela talks him into it, offering to train him. Bender soon figures out how the robot wrestling business works like and enjoys being rich and popular. But soon fame takes hold of him and he's about to pay the price for his behavior.
After Leela meets a man named Alkazar, she finds out she is not the only Cyclops left. Alkazar takes Leela to his home planet and proposes to marry her. Meanwhile, Fry suspects Alkazar is hiding something.
A meticulous substitute bureaucrat at Planet Express develops an unseemly attraction to dirty Fry while career bureaucrat Hermes Conrad goes to a vacation resort featuring forced labor. After Bender discovers the affair, only Hermes can save his personality after it is downloaded by the unscrupulous substitute.
In this episode of Futurama the Professor creates a What If machine that answers every question. The first question is what if Bender was 500 feet tall, the second is what if Leela was more impulsive, and the third is what if Fry never came to the future.
Fry and Bender enlist in the army to get a soldiers discount for bubblegum. When they are called to fight a war on a planet of bouncing ball aliens, Leela disguises herself as man to enlist with them. Bender is eventually sent to parley with the enemy, but this turns out to be a ploy.
Fry is reunited with his old girlfriend from the 20th Century, but she doesn't adapt to the 31st century as well as he has. Convincing Fry to return to the cryogenic chamber, they awaken in a barren wasteland and struggle to make a place for themselves.