
Milo and the Loose Tooth
Fable
Ages 6–8 · 8 min
A boy named Milo with a very loose tooth decides to enter a pre-negotiation with the tooth fairy by leaving a list of payment demands under his pillow.
Milo's tooth had been loose for three weeks, and he had opinions about it.
He had opinions about everything, actually. He had opinions about which cereal was the best (Honey O's, obviously, and anyone who said Cocoa Puffs was just wrong). He had opinions about the right way to tie shoes (bunny ears, not the loop-and-wrap — the loop-and-wrap was for people who enjoyed suffering). He had opinions about rain (against it), about Tuesdays (suspicious), and about the word "moist" (absolutely not).
Milo's tooth had been loose for three weeks, and he had opinions about it.
He had opinions about everything, actually. He had opinions about which cereal was the best (Honey O's, obviously, and anyone who said Cocoa Puffs was just wrong). He had opinions about the right way to tie shoes (bunny ears, not the loop-and-wrap — the loop-and-wrap was for people who enjoyed suffering). He had opinions about rain (against it), about Tuesdays (suspicious), and about the word "moist" (absolutely not).
But right now, his biggest opinion was about his loose tooth.
"It's not ready," he told his mom at breakfast, pushing it with his tongue so it tilted forward like a tiny drawbridge.
"It looks pretty ready," his mom said.
"It's not," Milo said. "I'll know when it's ready. It'll send me a signal."
"What kind of signal?"
Milo thought about this. "I haven't decided yet."
At school, his friend Priya showed him the gap where her tooth used to be. She'd lost it two days ago. She stuck her tongue through the hole and wiggled it around, which Milo had to admit was impressive.
"The tooth fairy gave me two dollars," Priya said proudly.
"Two dollars?" Milo pushed his own tooth with his tongue. It wobbled back and forth, back and forth, like a little fence post in the wind. "What did you spend it on?"
"Nothing yet. I'm saving up."
"For what?"
"I don't know yet. That's the fun part."
Milo didn't think that was the fun part. The fun part of money was having a plan. And that's when a thought landed in his head like a bird on a branch — a big, important thought.
What if the tooth fairy didn't give him two dollars?
What if she gave him one dollar? Or — and this was almost too terrible to think — what if she gave him coins? Just a bunch of coins rattling around under his pillow? Because Milo had another opinion: coins were the worst kind of money. You couldn't fold coins. They fell out of your pockets. They were heavy and clinky and you needed, like, fifteen of them to buy anything good.
But here was the real problem, the problem under the problem: Milo had no way to tell the tooth fairy what he wanted.
You couldn't write her a letter because you didn't know her address. You couldn't call her because she didn't have a phone number. You couldn't leave a note because — well, actually.
Actually, maybe you could leave a note.
That night, Milo sat at his desk with a piece of paper and his favorite green marker (another opinion: green was the best color for important documents). He chewed on the cap and thought very hard.
Dear Tooth Fairy, he wrote.
Then he stopped. He didn't want to be rude. Milo had been told many times that he came on "a little strong" and that "other people have feelings too, Milo." So he chose his words carefully.
Dear Tooth Fairy,
My tooth is almost ready. It is not ready yet, but almost. I wanted to let you know some things so we can be on the same page.
1. I would prefer paper money please. 2. No coins. Coins are heavy and they fall in couch cushions and then they're gone forever. 3. Two dollars is what Priya got so two dollars seems fair. 4. Actually could you do three dollars because I have been very patient with this tooth. Three weeks is a long time.
He paused. Then added:
5. Do you read these?
He folded the note and put it under his pillow, even though the tooth was still in his mouth. It was a pre-negotiation. Milo had heard that word on a podcast his dad listened to, and he liked the sound of it. Pre-negotiation.
The next morning, the note was still there. No response. Milo wasn't surprised, but he was a little disappointed. The tooth fairy clearly had poor communication skills.
At school, his friend DeShawn lost a tooth right in the middle of reading time. It just fell out onto his book. Everyone crowded around like he was a celebrity. Mrs. Patterson put it in a little plastic treasure chest from her desk — she had a whole drawer of those little treasure chests, which meant this happened a lot, which Milo found both fascinating and concerning.
"Did it hurt?" Milo asked.
"Nope," DeShawn said, grinning his new gap-toothed grin. "Didn't even feel it."
That night, Milo's tooth was really loose. Like, alarmingly loose. He could push it almost flat with his tongue. It was basically just hanging on out of stubbornness, which Milo respected, because he was also like that.
He stood in the bathroom and looked at it in the mirror. He pushed it forward. He pushed it back. He wiggled it side to side.
"Just pull it," his older sister Jade said, appearing in the doorway.
"No."
"I'll pull it for you."
"Absolutely not."
"You're being dramatic."
"I'm being careful. There's a difference."
"There really isn't," Jade said, and walked away.
Milo looked at his tooth in the mirror again. The truth was — and this was an opinion he didn't share with anyone — he was a little bit scared. Not a lot scared. Just a little bit. Because the tooth had been in his mouth his whole life, and once it came out, there would be a hole where it used to be. And even though a new tooth would grow in, it wouldn't be the same tooth. It would be a bigger, grown-up tooth. A permanent one.
And permanent was a very long time.
He went to bed with the tooth still in his mouth and the note still under his pillow. He added a line:
6. Still not ready. Stand by.
The next morning was Saturday, and Milo was eating an apple because his mom said he had to eat something healthy before he could have Honey O's (an unfair policy, but not the battle he was choosing today). He bit into the apple, and there was a tiny click, and something small and hard rolled across his tongue.
Milo froze.
He spit into his hand.
And there it was. His tooth. Small and white and a little bit yellow at the bottom, sitting right in the middle of his palm. It was — and this surprised him — tiny. This little thing had caused him three weeks of wiggling and worrying and pre-negotiation, and it was no bigger than a kernel of corn.
"MOM!" he yelled. "IT HAPPENED! THE SIGNAL! THE APPLE WAS THE SIGNAL!"
His mom came running in, and there was a lot of excitement, and Jade took a picture, and his dad said "Let me see, let me see," and Milo kept sticking his tongue in the gap and — oh. Oh, that was fun. That was extremely fun. He could feel the breeze through the hole when he smiled.
That night, Milo put the tooth under his pillow. He also put the note, but he crossed out everything he'd written before and wrote something new:
Dear Tooth Fairy,
Here is my tooth. I took good care of it.
Whatever you want to leave is fine.
— Milo
P.S. But not coins.
He couldn't help it. He was Milo. He had opinions.
The next morning, he reached under his pillow and found two crisp dollar bills and a small piece of paper, pale blue and no bigger than a sticky note. On it, in tiny, sparkly handwriting, it said:
Dear Milo,
I do read these.
— T.F.
Milo held the note up to the light from his window. The letters glittered. He smiled his new, gap-toothed smile — the kind of smile that lets the breeze right in.
He taped the note to his desk lamp where he could see it every day.
And he only had one opinion about it: perfect.



