Although the tooth-fairy part has been fun, getting Jessie’s teeth out has involved lots of unwanted drama. I’m surprised the tooth fairy has had any emotional energy left to do his job.

Jessie has always made such a big production when she has loose teeth that I was shocked when she walked into my home office one recent evening with a large molar in her hand and a tissue in her mouth. I had missed not only the preview, but the entire dramatic movie produced by and starring my daughter. I thought, This is too good to be true! Only two to go.

Little did I realize that, though I may have missed the tooth-pulling drama, the entertainment had yet to begin. Since my wife, Mattie, was out of town for a couple of days, tooth-fairy duties fell solely on me, which in teeth past, hadn’t been a problem. However, Jessie, knowing the identity of the tooth fairy and having only a few more opportunities to play along, wanted to keep things challenging. She achieved her goal.

Jessie is a sound sleeper. I think I could crash cymbals above her head and, come morning, she wouldn’t know a musical performance had taken place. On tooth-fairy night, I didn’t have cymbals, only a five-dollar bill. There certainly has been inflation since the tooth fairy brought me 25 cents.

I snuck into Jessie’s room and gently placed my hand under her pillow and around, over, under, and between numerous stuffed animals. First attempt – nada. Second try – nothing but a monkey’s tail. Third attempt – still no plastic bag with a big molar in it.

Jessie had informed me prior to going to bed that she planned to “hide it well.” She did!

My texts to Mattie at 11:04 p.m. summed up my situation. “I searched and searched and searched. Love, the defeated tooth fairy.” “She told me she was going to hide it inside one of her stuffed animals, but then thought that would be too hard for the tooth fairy to find.”

Not one to give up, I made a final attempt before heading to bed. Strike four!

My text to Mattie at 11:23 p.m. read, “The tooth fairy tried one more time. I bumped into the end of her bed. I bumped into her three-way floor lamp. She’s a sound sleeper. I reached under all her pillows and lifted a few stuffed animals. I picked up her pet pillow. Nothing! Then, she groggily opened her eyes and gave me a weak ‘hi’. She held out her hand with the baggie in it. She was holding it! Love, a worn-out tooth fairy.”

Though this tooth fairy doesn’t carry a wand, my baby-tooth collection record was perfect to this point. I made a final attempt at 1:38 a.m. Jessie looked so angelic as her hand rested under her head. I reached under her pillow and performed a thorough search, but for the fifth time came away without the prize.

She won. I went to bed.

When Jessie awoke in the morning, she asked, “Why didn’t the tooth fairy come?” She knew I’d try again. She said that after she caught the tooth fairy in action, she made it easier by leaving a small portion of the baggie stick out from under the pillow. Apparently, she laid on it.

That night, Mattie, who had returned from her trip, took her turn as tooth fairy. Mattie waited on the sofa and thought she had it made when Jessie went to the bathroom. She raced into Jessie’s room and searched under the pillows. However, Jessie, expecting her mom would take the opportunity, had taken the baggie containing the molar into the bathroom with her.

Later that night, having fallen asleep on the sofa, Mattie woke up and fulfilled her tooth-fairy duties. Jessie made five dollars while providing our family with some special memories.

Mattie and I are only two baby teeth and $10 away from retiring our wings, which is bittersweet. We won’t miss the tooth-pulling drama, but all three of us have cherished the tooth-fairy adventures.

Maybe I had the prize, much bigger than a molar, all along.