The screeching halted our conversation and made us scan the playground for the site of the commotion. “Eeeeeeee! Wooooooo!” My friend’s six-year-old daughter Clara had burst into a joyous victory lap around the playground, her face beaming with excitement. A trickle of blood connected her mouth to her chin. Unconcerned, Clara lifted her arms in triumph, displaying for the other playground kids the prize pinched between two of her fingers: her first lost tooth.

The children watched Clara’s slow jog, oohing and aahing in turn. Clara’s mother and I stood and applauded from an adjacent bench. Clara pumped her fists at us in appreciation.

That’s when I noticed my own six-year-old daughter hiding under the clubhouse, hugging her knees and sobbing. Minutes prior, my daughter and Clara had been busy playing travel agency inside the clubhouse, booking extravagant vacations for pretend clients, before Clara’s loose tooth finally released its hold.

“What’s wrong, honey?” I asked, bending to eye level with my daughter.

“Clara lost (sob) her tooth before me,” my daughter bemoaned in spurts. “I’m turning seven before her (sob) and the Tooth Fairy forgot that. Now me and Clara are out of order. It’s not fair! (wail).” My daughter buried her head in her knees, blaming the tiny winged fairy for swindling her out of a victory my kid thought she had won by virtue of sheer birth-order.

“Well, it’s just not your turn yet to lose your first tooth,” I said a little too matter-of-factly. “Please wipe your tears and go congratulate Clara on her special moment.”

As my daughter mulled over what I hoped was an empowering life lesson that she’d absorb and thank me for one day, a creeping awareness of my own hypocrisy gripped me. Was I the type of person who lived life instantly high-fiving everyone who got something I wanted, unbegrudged? No, I was not.

Long-buried memories appeared before my mind’s eye, resurrecting scenes in which I had let envy keep me from congratulating others for their accomplishments.

My thoughts yanked me back to high school. A classmate had just bested me for tenth place in our graduating senior class by a hundredth of a GPA point. The classmate, a quiet girl with few friends, had always been kind to me. Despite that, I recalled responding to her (deserved) win with a huffy silence that left her alienated and hurt for the remainder of senior year.

I tried blinking away the feelings of remorse that began to jab at me over my childhood pettiness. However, my conscience wasn’t done with me yet.

Another image materialized to highlight my cavalier expectations of my six-year-old. In that recollection, I was at my first job out of grad school. I watched as a co-worker landed a promotion for which I had been vying.

My co-worker was the type of guy who berated assistants in the hallway; I did no such thing. My co-worker siphoned credit from his peers in trickles and chugs; I did no such thing. My co-worker brought in a consistent stream of business; I did no such thing or, at least, not as consistently as he did. Given his greater contribution to our company’s bottom line, my co-worker ascended the notch up the corporate ladder.

Me? I got a cringe-worthy memory of avoiding eye-contact with my new boss and simmering in my office for days after.

The injustice of my co-worker getting a promotion despite his being the office sleaze wasn’t the point. The lesson in that memory and the one before it was that I would live to regret such inelegant refusals to congratulate peers.

“Man, I was a jerk,” I whispered, still sitting on my haunches.

“What’s a ‘jerk,’ Mommy?” My daughter’s wide-eyed question pulled me out of my head and back onto the playground woodchips.

“‘Jerk’ is a not-nice word that you shouldn’t say,” I said in a breath, feeling a sudden urgency that my daughter learn to stem future regrets, as well as a renewed understanding that doing so isn’t so easy. “If you’re up for it,” I took a second stab at advising, “will you please go congratulate Clara on her happy moment? I know it’s not easy, but you may feel bad about it later if you don’t.”

My kid gave me a half-smile in response and shuffled her light-up Sketchers in Clara’s direction. I fretted until I heard my daughter mutter a sincere-enough “That’s awesome” to her pal. That’s my girl.

Moments later, the fallen tooth was forgotten. The two girls had resumed their gleeful game of travel agency, albeit with a new lisp for one of the agents, and an avoided future regret for the other.