Full Disclosure: A Face Only a Mother Could Love  

Truth to be told, each fall I anxiously await the arrival of my kids’ annual school photos—it’s my guilty pleasure. 

Pioneer chic at its finest. Wagon Wheel or bust.

There is nothing more amusing than peering through the envelope’s acetate preview window to find a ‘retake’ glaring back, silently screaming for help. I have seen my fair share of horrific phot-ohs, both of me, personally, and my offspring. Naturally, the apple does not fall far from the photo booth.

Year after year, school pictures are the gift that keeps on giving—a constipated smile, a rogue snaggletooth, a set of firmly closed eyes, or even an unfortunate Nutella smear around the mouth. Been there, done that. 

Last fall, my son’s picture was taken almost immediately after running the timed mile at Saxe. At the portrait session, he was well beyond the point of exhibiting a healthy, dewy glow. His flop sweat was worthy of a Saturday Night Live news anchor sketch. Plus, the kid was too far gone for the 1970’s back-pocket comb that was provided to remedy the situation. He would know how to better handle a power saw than a fine tooth comb. That day, the mile won—and I have the photo to prove it.

Skeeter the Muppet.

I cannot help but chuckle and reminisce over the horrendous photos that I have personally taken over the years. My mug wreaked havoc from South School until my NCHS senior portrait, the pièce de résistance, thanks to my Flock of Seagulls bangs. During the elementary years, I got away with clinging to babyish cuteness. But, man, those middle school years are tough to look at. After being lovingly branded “Skeeter” by my French teacher, I was seriously busy working on my personality from 6th through 12th grade.

Black eye on right. My mother made an attempt to use concealer.

To this day, my school photo Hall of Shame is showcased at my mother’s house (I’m pretty sure The Glass House Tour sells 2-for-1 tickets during the off-season). Most notable is the picture in which I had a black eye from sliding face-first into an organ. Don’t ask. If that didn’t warrant a retake, I don’t know what did. My folks were clearly trying to keep me humble and provide fodder for future therapy sessions. Also, I place a significant amount of blame on Dorothy Hamill and her wedge haircut for ruining any attempt at a flattering photo from 1980 to 1987. I never stood a chance.

These days, school photography is a big business. Companies are savvy and have dramatically increased profitability over the years. New Canaan parents can opt to retouch blemishes (perhaps a black eye?), even out skin tone and whiten teeth. What I would have done to FaceTune and de-Skeeter-ize my old yearbook photos. I’m pretty sure the term “a face only a mother could love” was coined after my 4th grade photo went old-school viral.

Can’t get enough wagon wheel.

Luckily for this generation, photo-taking artistry has taken a giant leap in the right direction. A wide array of backdrops are now available to set just the right tone, thanks to greenscreen technology. Long gone are the days of standing in front of a poster of a tree while casually embracing a wagon wheel. Pioneer chic has had its last day in the sun. From the looks of it, our kids have it pretty good.

If selecting just-the-right backdrop isn’t exhausting enough, there are a multitude of package options, which all seem to include the wallet sized pics that no one wants. There is no way around the wallet photos—believe me, they will get you. It’s clear that math wizards, who specialize in outsmarting the intellectually average consumer, have been hired to calculate every possible package permutation to create mind-boggling photo bundles that are somehow more economically attractive than simply selecting the three photos that you really want to buy à la carte. Deluxe Package, you get me every time.

A potpourri of unfortunate school photos throughout the years.

Right on schedule, this year’s school photos arrived a couple of weeks ago, and to my horror, they were picture perfect. Imagine my confusion and disappointment. I’m assuming retake day will somehow go on as planned without us. To those more fortunate, I will miss the giant adrenaline rush that retake day provides—it’s a high-stakes game and the last shot at a decent, widely circulated photo. 

As an expert, my advice is to exude confidence, lay it all on the table, and go “all in.” I am extending my very best wishes (and a perfect hair day) to the students who are betting it all on one last take. You got this.