Picture this...

In a digital age, you'd think school photos would be a snap.

My youngest son's first-grade teacher stifled a giggle as she handed me an envelope of school pictures, discreetly turned image-side down. "You have to see this."

I flipped over the envelope. The photo in the glassine window showed my little guy frowning deeply, chin sunk against his chest and pupils rolled up as if he were inspecting the underside of his eyelids. The effect was a menacing glare you might find on one of those black-and-white-movie monsters, right before it bites off a chunk of skyscraper.

A girl squeezed between me and the teacher to sneak a look. "Ewww. He looks creepy."

I hid the envelope against my jacket and tried to ignore the smiling images being stuffed into backpacks all around me. "So when are retakes?"

Monster faces aside, I've always liked school pictures. There's something appealing about those tiny rectangles of photo paper marking the progression of time, teeth, and haircuts against a simple backdrop. As children gradually transform into their adult selves, some things remain constant – a persistent cowlick, an enduring flicker of personality, that same beautiful smile.

Unfortunately, the smiling part is a problem for my kids. Our personal photos, many of which appear to record a sullen and joyless childhood, could easily inspire captions like "Doing time in kindergarten" or "Hating Yellowstone." But they're just a reflection of how my sons feel about being photographed. For them, nothing extinguishes a smile faster than a camera. And when there's a strange adult behind the viewfinder, my boys are only slightly more likely to produce a pleasant expression than the elementary school classroom pets, most of which are reptiles (and introverts as well, now that I think of it).

I've helped out a couple of times on school picture day, and I know it's hectic. In just a minute or so, photographers must pose each child, make a connection, elicit a smile, and take a photo worthy of Grandma's fridge. With digital cameras, they can preview the images to ensure a good result. But the new technology is a mixed blessing for smile-resistant subjects like my kids. With film cameras, photographers could hope for the best and move on. Now they have to keep trying.

My firstborn, a cooperative but suspicious kid, once came home from school picture day disturbed by a photographer's increasingly desperate attempts to win a smile. Extreme silliness, in his view, could not be trusted in an adult. Eventually he had bared his teeth and turned up the corners of his mouth so he would be allowed to escape. The final result may have even qualified, technically, as a smile. But it was the kind you might give a wisecracking nurse holding a hypodermic needle against your arm. In the photo, his mouth seems to say "please" while the rest of his face says "get me out of here."

His little brother, the one with the villainous expression, resisted more consciously. He had been tricked into showing dimples for kindergarten photos, in direct violation of his personal code, and all the Christmas ornaments and school mementos now bearing his smile only strengthened his determination to withhold it. But when I got back the scary first-grade picture, I was still surprised. With the ability to shoot and preview multiple images, the photographer had settled on this one. It was a clear sign of surrender.

I sent my son for retakes, adding a scribble to his order form: "It's OK if he doesn't smile." The replacement photo was an improvement, a serious-looking pose that made him look "like Steve Jobs without the glasses," according to his teacher. It gave me hope for the next round of pictures in the spring – maybe we could progress to a lip twitch, or even a smirk? But when spring came, my reluctant kid produced another mug shot guaranteed to frighten small children – other small children, that is. The smile waiver had stopped working.

Recently a backpack search for a missing peanut butter sandwich turned up a crumpled flier for yet another school picture day. I wasn't worried about my fifth-grader, who had learned to fake a smile just convincing enough to keep the line moving. But I knew it would be tough for my little guy.

When I dropped him off at school that day, I watched other parents tame flyaway hair and scrub milk mustaches while they reminded their children to smile pretty. But my priorities were different. As my son hitched up his pack, I leaned over and whispered in his ear.

"It's OK if you don't smile, buddy. Just try not to look evil."