When my oldest lost his first tooth, I had grand ideas. The magic! The fun! The excitement! So after he decorated his little envelope, tucked his tooth carefully inside, and slid it under his pillow with barely contained anticipation, the tooth fairy made her debut.
And she decided to go big.
Not just a dollar but also a tiny bag of Legos. Because he loved Legos, and it was adorable, and I thought exactly zero steps ahead.
Here’s the thing nobody reminds you when you’re standing there in the glow of your firstborn’s gap-toothed smile: that child is the oldest of four. Four children lose a collectively staggering number of teeth. Eleventymillion, to be exact. And the tooth fairy, bless her ambitious little heart, had set a precedent she would suffer to maintain.
The real problem isn’t the toy, though the toy is definitely a problem. The real problem is that teeth fall out without notice. There’s no preview, no calendar reminder, no grace period between “Mom, it’s wiggly” and “Mom, it came out” — and suddenly it’s 11pm and you’re standing in your kitchen in the dark, remembering that the crisp dollar bill you were saving for exactly this moment was actually scrounged and sent in for a field trip two weeks ago.
The one you told yourself you’d replace.
You did not replace it.
And now you need not only that dollar but also a small, fun toy. Which, fine, maybe you have one squirreled away somewhere. But small toys come in small packaging, and small packaging is inexplicably the crinkliest material known to mankind. In daylight, it’s nothing. At midnight, creeping down a hallway toward a room shared by two children, it is a five-piece percussion ensemble.
I have military-crawled across a bedroom floor. I have laid flat in the dark next to a child’s bed, hand frozen mid-reach beneath the pillow, listening to them stir and praying with everything I had that they would not open their eyes. And wondering, in that moment, what exactly I would say if they did.
“Oh hi, sweetie. Just lying here on the floor. In the dark. Go back to sleep.”
And then there was the night we came home from a holiday party.
The babysitter met us at the door with the cheerful news that a tooth had fallen out that evening and was already tucked under the pillow, waiting. I stood there in my coat, still holding my clutch, doing the math.
Tooth fairy. Tonight. Now.
Also — and this is important — the Elf on the Shelf had not moved, and if the elf doesn’t move, the entire mythology begins to unravel in a completely different direction.
I will not pretend I was fully sober. Those chocolate martinis were delicious.
My husband declared himself second in command and promised to stay awake with me until the mission was complete. He was asleep and snoring within minutes.
I made three attempts on my own –three– before retreating each time because someone stirred, or the crinkle was too loud, or the one time he did wake and I blurted out that I was just checking to see if the tooth fairy had come yet too.
By 2am I was perched on the edge of my bed nearly in tears, mascara and hairspray everywhere, negotiating with myself about whether children actually remember these things or whether I could plausibly claim the tooth fairy had simply had a busy night.
I decided she did not have a busy night.
She had one job, and she was going to do it.
I finished the mission just before dawn. I know this because I had barely closed my eyes when the kids came crashing into our room (delighted, loud, holding up their findings) and also requesting breakfast.
So here is my best unsolicited advice to every mother of a child with even one loose tooth: buy the tooth pillow now. The kind with the little pocket that hangs on the outside of the bedroom door. Before the first tooth falls out. Before you set any precedents involving Legos.
It’s still magical. A glittery dollar tucked into a tiny velvet pocket is genuinely delightful, and your child will not be scarred by the absence of a surprise toy at midnight. You’ll sleep better. You’ll stay off the floor.
And the tooth fairy can finally retire her tactical crawl.
These are some cute options to get you started. Buy one for yourself, give one as a baby gift, give one to the kid entering the loose-tooth years. Keep one in the gift closet. Trust me on this one: friends don’t let friends military crawl in the dark!

