Every time I see this photo my heart breaks again. He was desperate to loose his first tooth. His brother had been doing it for years. He said if my tooth falls out today, I get three hot dates with you. Of course I agreed because it seemed like a would win in this situation. Adventure with him was always fun for me and I’d honestly give him all the hot dates for free. He disappeared into the bathroom. 15 minutes later I tapped on the door to see if he was okay. He said “I’m fine mom.” Ten minutes later I asked again. Then nearly 45 minutes from entering the bathroom he emerged triumphantly with tooth in hand. He held it out to me and immediately burst into tears. “I don’t want my tooth to be out he wept.” He was heartbroken. He cried desperately for what felt like a lifetime but might have been closer to 20 minutes. I held him. It was one of those moments where I couldn’t undo or fix things I could only witness the grief. The tears did stop. The potential for a cash gain from the tooth fairy arrived (and trust you me the tooth fairy was ready to handy over a a pretty penny at this point) and promises of fun times doing whatever he chose together settled in so the tears could abate. That is when this photo was taken. The moment after all of that. Each time I see it, I find the evidence of his tears in his eyes and I feel all over again. Reminding me how often a moment can hold both great triumph and deep sorrow.