A Trusted Friend in a Complicated World

10 Hilarious Tooth Fairy Stories That Will Make You Laugh Out Loud

We dare you to read these silly, sweet stories and not crack a smile.

1 / 11
child sleeping

A tooth fairy’s job ain’t easy

Not only must the tooth fairy work without ever being detected—no small feat given that she’s reaching under pillows—but she has to do this many times during a child’s life (20, to be exact). Lest she elicit outrage, she also needs to keep up, money-wise, with the other parents, er, fairies. (According to a Delta Dental poll, the Tooth Fairy is now handing out an average of $3.91 per tooth.) Here, Reader’s Digest readers share 10 silly, sweet stories of kids’ firsthand fairy experiences.

2 / 11
mother son

Winging it

One night, my seven-year-old son, Daniel said to me, “Mom, I know it’s not true about the tooth fairy. My friends told me.” “Uh…” I stalled. “Is it true, Mom?” he asked. “Is it you? Just tell me.” “Yes, Daniel,” I replied. “Really?” Daniel asked, wide-eyed. “Are you serious?” “Yes,” I replied. “Wow!” he exclaimed. “Where do you hide your wings?”
Check out these hilarious quotes from real moms.

3 / 11
Pile of Coins

Is there a return policy?

When his two front teeth fell out within days of each other, my six-year-old son, Joey, was delighted by a quick and profitable succession of visits from the tooth fairy. However, the novelty of having a wide gap in his smile quickly paled. Not long after, while my husband was tucking him into bed, he found two coins under Joey’s pillow. When asked what the coins were for, Joey replied firmly, “I want my teeth back.”

4 / 11
5 dollar bills


I was playing tooth fairy when my daughter suddenly woke up. Spotting the money in my hand, she cried out, “I caught you!” I froze, trying to think of an explanation for why I, rather than the tooth fairy, was depositing a gift under her pillow. I was let off the hook when my daughter interjected, “You put that money back! The tooth fairy left it for me!”
Every parent will appreciate these hilarious true parenting stories.

5 / 11
Mother and daughter hugging
iStock/Bogdan Kosanovic

The fairy next door

One day when I picked up my four-year-old daughter, Kirsten, from the bus stop, she told me that a friend on the bus had said her mom was the tooth fairy. I was casting about for an explanation when Kristen gave me a huge smile and said, “Can you believe it! The tooth fairy lives right down the street from me!”

6 / 11
child sleeping

A dark truth

I realized that at the age of seven it was inevitable for my son to begin having doubts about Father Christmas. Sure enough, one day he said, “Mum, I know something about Santa Claus, the Easter Bunny, and the tooth fairy.” Taking a deep breath, I asked him, “What’s that?” He replied, “They’re all nocturnal.”

7 / 11
iStock/Thomas Faull

A foolproof fairy

My friend’s daughter, Chelsea, found a baby tooth that her kitten had lost. She and her sister decided that they could put one over on the tooth fairy. That night they placed the tooth under Chelsea’s pillow. And it worked—to a point. But the tooth fairy left a can of sardines. Check out these funny fibs real parents have told their kids.

8 / 11
Dental treatment
iStock/Dmitriy Shironosov

Dental deity

My five-year-old Alphonse has cavities and often has to visit the dentist. I didn’t realize how concerned he was about the expenses until he told me, “Mom, you know why the tooth fairy gives money away? So that it will help us pay our dentist.”

9 / 11
Cute little girl sleeping

It pays to be the youngest

At five I was the youngest child around when Uncle Richard, Aunt Sally, and their teenage kids came to visit my family one summer. One night during their stay, I lost my first tooth! I headed up to bed, tucking the tiny thing under my pillow before turning in. Little did I know that everyone in the house was afraid my parents would forget the occasion amid the excitement of having guests. So they all decided to take matters into their own hands. First my parents sneaked in to make their deposit. Rewarding me with some of their hard-earned money, my four teenage siblings, were next, followed by my cousins. After Aunt Sally left several dollars, Uncle Richard took his turn. You can imagine my delight the next morning when I lifted my pillow to discover that the tooth fairy had left me a small fortune—it even included a $20 bill! I scooped up the cash and ran downstairs to tell everyone. They were all speechless, but I barely noticed. When I went back upstairs to count my loot and deposit it in my piggy bank, I heard a roar of laughter coming from the kitchen. To this day, I wonder how so many people sneaked into my room without waking me—and without running into each other in the hallway!

10 / 11
little girl loses her baby teeth

Never giving up

One day, while I was catching up with my seven-year-old granddaughter, Dia, on the phone, she told me she had lost her two front teeth.  I asked if she had got a visit from the tooth fairy. Dia told me with the first tooth, she had put it under her pillow and when she woke up in the morning, the tooth fairy had left money but had taken her tooth. “When I lost the second one,” Dia said, “I wrapped it up really good and hid it in my drawer. There’s no way the tooth fairy is going to get any more of my teeth!”
These are the funniest mistakes kids have ever made.

11 / 11
sellotape, scotch, painter and duct tape on a white background
science photo/Shutterstock

The fairy writes back

When our daughter, Genevieve, was nine, she loved duct tape. She was also at the age when she questioned the existence of the tooth fairy. When she lost another tooth, she thought she’d be a smarty-pants and catch the fairy. That night, my husband, Matt, and I entered her room. To our surprise, we found reams of duct tape fastening her tooth to her hand. Unable to remove it, we left money under her pillow, knowing we’d have to come up with an explanation. The answer came to me: I’d have the tooth fairy write her a letter. Since she’d recognize Matt’s handwriting and mine, I asked a coworker to write it. Little did I realize what a great letter my coworker would write. The letter said that the tooth fairy was giving Genevieve the benefit of the doubt; since she must have “accidentally” wrapped her tooth in tape, the fairy left $2 as a “token of our goodwill.” But the tooth fairy went on to say, in no uncertain terms, that if she did not get the missing tooth by Friday, the Easter Bunny—the tooth fairy’s associate—would be paying Genevieve a visit. The next night Matt and I left the letter under Genevieve’s pillow, and in the morning, we realized what we had done. Not only did she think the tooth fairy was real, she also believed that the Easter Bunny was out to get her.

Next, check out these adorable tooth fairy traditions to try the next time your kid loses a tooth.