We’ve been waging war with a particularly stubborn bottom front tooth for what seems like eternity. Oliver either literally has the world’s longest baby tooth root system, or has secretly superglued his teeth to his gums.

We’ve tried everything, but apparently this particular tooth is very special to Oliver as he refuses to allow anything near his face that might cause the minute chance of it dislodging from his mouth.

After all the tears… the refusing to eat anything that’s not yogurt… the constant vigilance and keeping his head on a swivel as to ensure nothing could or would knock out his tooth it was time.

Sadly, even with all of the added protection, a loose tooth sometimes just has to loose tooth. That little chiclet choose 8:30pm on a Wednesday night to just be free and live it’s best life.

… thank God for that!!

And with that being said, the tooth is sealed and ready for the Tooth Fairy.

Interestingly, the tooth has been placed under the spare bedroom pillow, not his own. He claims it’s so it doesn’t get lost. (AKA: he’s scared shitless of the tooth fairy).

Hopefully the Tooth Fairy comes through because Oliver thinks he’s getting $100, baseball cards… AND. I. QUOTE.: “A CVS credit card.