All of a sudden, Milo is driving along a strange country highway. He can’t see his room or the tollbooth—this is real. Milo is confused. The only thing he knows for sure is that it’s a nice day for a trip. It’s sunny and the colors seem rich and bright. As Milo drives, he comes to a sign that welcomes him to Expectations and instructs him to park and blow his horn if he’d like “information, predictions, and advice.” Milo follows the directions.
Prior to going through the tollbooth, Milo’s imagination was more or less nonexistent. But now that he’s agreed to play along and go through the tollbooth, his imagination has symbolically cracked wide open. This is confusing for Milo, and he assumes that what he’s experiencing must be real, since this is perhaps his first time engaging in this kind of imaginative play.
A small man hurries out of a house. He speaks quickly and repeats everything he says multiple times. In this manner, the man welcomes Milo to Expectations and introduces himself as the Whether Man. Shocked by the greeting, Milo asks if he’s on the right road for Dictionopolis. Confusingly, the Whether Man says that there are no wrong roads to Dictionopolis; it’s the right road if it heads to Dictionopolis. Otherwise, it’s the right road to somewhere else. The Whether Man asks if Milo thinks it’ll rain.
Milo is so uptight and sensible that the Whether Man’s strange manner of speaking is just beyond understanding. The Whether Man is somewhat confusing, but he also encourages Milo to be open to possibilities. Milo might not get where he initially wanted to go on this road, but he might still end up somewhere just as interesting.
Extremely confused, Milo says he thought the man was the Weather Man—but the man says he’s the Whether Man because “it’s more important to know whether there will be weather than what the weather will be.” At this, he releases balloons into the air to see which way the wind is blowing. Milo asks what Expectations is like, and the Whether Man explains that everyone has to go to Expectations before they get where they’re going. His job is to hurry people along, and he asks how he can help Milo. But before Milo can ask another question, the Whether Man runs away to fetch an umbrella.
This passage is humorous because “weather” and “whether” are homophones, words that sound the same but are spelled differently and have different meanings. It’s unclear if Milo understands what exactly the Whether Man is even saying, since unlike readers, Milo can’t see the words written differently on the page. This lets readers in on a joke while making Milo the butt of the joke. Milo’s confusion can also be read as a consequence of his unwillingness to learn anything in school.
Though Milo doesn’t know where he’s going, he tells the Whether Man he can find his own way. The Whether Man asks Milo to return his way if he finds it; he lost it years ago. He opens the umbrella and says he hates making decisions, so he’s glad Milo decided to leave on his own. He believes in expecting everything, so nothing unexpected ever happens. Suddenly, it starts to rain over the Whether Man.
Again, the Whether Man’s joke about getting his way back is funny for readers, as he’s using wordplay to make the idea of “finding his way” literal rather than figurative. But because Milo doesn’t know how to use language well enough, it’s lost on him. It's also hard for Milo to take the Whether Man’s advice to expect everything, because Milo doesn’t have much of an imagination. If he can’t imagine multiple scenarios, it’s impossible to foresee lots of things.
Milo drives away into a green valley. As he drives, Milo tells himself that the Whether Man is the strangest person he’s ever met. (Milo doesn’t know he's going to meet many more strange people shortly.) As he drives, he daydreams and stops paying attention to where he’s going. This causes him to take a wrong turn. Things immediately begin to look gray, and the road becomes boring. The car gradually slows down until it comes to a stop. Worried, Milo asks where he is. A voice answers that he’s in the Doldrums—but Milo can’t find the voice’s source. Milo fearfully asks what the Doldrums are, and another voice says it’s “where nothing ever happens and nothing ever changes.”
Because Milo doesn’t have much practice using his imagination or noticing things around him, the Whether Man is “strange” (rather than funny, as he is for readers). This is, per the novel, also why Milo starts to daydream and stop paying attention here. He’s not practiced in staying engaged with anything for any length of time. And this, the novel warns, can lead to winding up in places one might not want to be, such as the Doldrums with these frightening, mysterious voices.
Milo realizes the voice came from a tiny creature sitting on his shoulder. It blends in with his shirt. The creature introduces all of his kind as the Lethargians. Milo notices lots of creatures like the one on his shoulder. They all blend in with whatever they’re sitting on, but otherwise look exactly the same. Milo asks if they could help him, since he thinks he’s lost. But another Lethargian tells Milo not to say “think”—it’s against the local rules. When prompted, Milo looks this up in his rule book: thinking isn’t allowed in the Doldrums. Milo says that’s ridiculous since everyone thinks, but the Lethargians say that Milo wasn’t thinking—that’s why he’s here.
To readers (and to Milo), it probably seems ridiculous to outlaw thinking altogether—after all, everyone is thinking all the time. But the Lethargians are actually talking about active thinking here—they don’t consider daydreaming to be real thinking. The Lethargians are another example of humor in the novel, as their name derives from “lethargic,” or lazy. When Milo chooses to push back on the Lethargians, it again shows that he’s practical. But the Lethargians are also highlighting for Milo some of Milo’s faults, such as that he can’t pay attention for long periods of time.
When the Lethargian falls asleep and falls off the flower he’s sitting on, Milo laughs. Another Lethargian tells him laughing is also against the rules in the Doldrums. Then, another Lethargian shares the daily schedule in the Doldrums. It’s packed with napping, daydreaming, dawdling, putting things off, and “loafing.” All of this means that they “never get nothing done.” Milo objects that they never get anything done, but a Lethargian snaps that they don’t want to get anything done. Another invites Milo to join them on holiday (where they do nothing). Milo agrees.
Laughing and finding something funny requires thinking; things read as funny when they’re somehow incongruous or there’s a punchline to decipher. So, banning laughter is another way to ban thinking. Interestingly, the Lethargians’ daily schedule reads a lot like what Milo’s schedule at home seemed to be. Milo didn’t do anything and seemed pretty content to keep doing nothing. He daydreamed, was bored, and put off doing anything important (like learning).
Yawning, Milo asks if everyone really does nothing. A Lethargian says that everyone except the watchdog does nothing. Another Lethargian shrieks that the watchdog is coming, and all the Lethargians scatter. Milo’s eyes go wide as a big dog skids to a stop in front of him. The dog looks normal—except his body is a ticking alarm clock. The dog asks Milo what he’s doing here and howls with rage when Milo says he was “killing time.” Milo explains he was on his way to Dictionopolis and got lost. He asks for help.
From the beginning, the watchdog establishes himself as in conflict with the Lethargians. While they endeavor to do nothing, the watchdog’s whole purpose is to prevent people from wasting and even “killing” time. His ticking alarm clock body symbolizes the idea that time is always ticking, even if people aren’t aware of it. In addition, the watchdog is another character whose name involves wordplay—he is literally a clock combined with a dog, rather than a guard dog.
The dog says Milo has to help himself; Milo must know why he got stuck here. Milo says he wasn’t thinking, and the dog says that obviously, Milo has to start thinking again to get out of the Doldrums. With that, the dog hops into the car and asks to join—he loves car rides. Milo has to try hard to think, since he doesn’t do it often. But as he thinks, the car picks up speed. Milo finally reaches the main highway, marveling that he can do so much just by thinking a bit.
Here, the novel confirms outright that Milo doesn’t think much. So, having to think to get out of the Doldrums is entirely new territory for Milo. Milo shows that he’s more than capable of changing his ways when he sees how effective putting his mind to something can be. And the novel injects some humor when the watchdog asks to accompany Milo for a car ride, as this is an activity that most pet dogs enjoy.