No one likes taking school pictures because it's almost impossible to take a good one (based on my past experiences). And when picture day rolls around you have a 50% chance of having a good photo. But for these people, lets just say their chances were much lower.
Identity Swap

“In his freshman year my brother (a white dude) switched his picture card with an Asian friend of his. They figured that the picture guy would notice that it was weird that a white guy would have an obviously Chinese name, and they would tell them to switch back.
Nope, for the rest of his time in high school on every form and computer system my brother was an Asian guy. Confused the h-ll out of substitute teachers” (Source).
That Was a Tough Photo Session

“I was photographing a 3rd grade class and I got to an adorable little boy and went through my list of instructions; ‘now turn your head here, shoulders here, oopsie, your right arm there. Wait. Please move your right arm.’ He gave me the saddest little look and showed me the stub on his right shoulder. He had no right arm. I felt like a terrible person” (Source).
I Work Here

“We were doing photos at a special needs high school. Guy comes up in a windbreaker, corduroy high water pants, velcro tennis shoes and the thickest glasses I’ve ever seen. I asked him whose class he was in so i could make sure he was in the right group and he said he wasn’t a student, he worked there” (Source).
But I’m Not Sick

“I’m not a photographer but I probably gave the one who took my second grade school photo a weird feeling. I’d just moved from a third world country and didn’t speak a lick of English. I had no idea what a soda can was, much less the hallowed tradition of Picture Day. So when my class was directed to shuffle down the hall in an orderly line to the gym, and I saw all those abstracty bluish background canvases that looked like X-ray images all over the gym… and that we were all going towards a spot directly in front of it, one at a time, in this solemn fashion –I thought we were all, one by one, having a medical procedure done to us. And that’s why I look a little teary and very, very stoic in my second grade photo. There’s a framed copy of it at my parents’ house” (Source).
But It’s My Best Fox Suit

“Some kid showed up in a fur suit. Like, full on fur suit. A bright blue fox, and he ended up having a half hour long argument with the photographer and assistant principal over it” (Source).
You’re Such a Brave Boy

“So I’m in kindergarten getting my picture taken (1980) … The flash bulb pops and explodes, catches that umbrella thing on fire. All the teachers scream and I sh-t my pants….. Awkward when I get picked up by mom wearing underoo’s and holding a plastic bag …. But the teachers said I was brave …. Ahhh simpler times” (Source).
Please Don’t Smile

“I worked for a company that did this. Didn’t work there long but the worst thing I encountered was multiple notes on the forms parents sent back to us saying ‘Don’t make my child smile.’ or ‘They have a bad smile don’t make them smile.’ How terrible is it to tell strangers you hate your child’s smile?! I understand some didn’t want big toothy grins because they were missing teeth, but that’s part of childhood. They’ll never be like that again. Why not enjoy it?” (Source).
You Blinked Again

“Spent 15 min with a guy because he blinked every time I took the photo. I tried everything in my book, making him close and open his eyes before snapping the picture, delaying the flash, shooting without flash, taking the picture while talking to him so he’ll be distracted. Nothing worked. Ended up taking his picture with a cellphone, because apparently what made him close his eyes was the shutter/mirror sound” (Source).
That Outfit Won’t Work

“It was for a middle school. There was this young lady having her portraits done. She wasn’t doing anything bad in hindsight. She was just very well developed for her age and the shirt she was wearing had a little cleavage. I’m sure her parents sent her out of the house just fine, and she probably felt very pretty and confident. Young lady, having photos done, no big deal. Class portrait time – out of nowhere this middle aged female school administrator comes up to her. She yanks her out of the photo and chastises her for her outfit. Then she makes her wear this oversized baggy t-shirt and we redo the photo. I can only imagine what this girl was going through” (Source).
Dear Ms. Judy… You’re the Best Teacher Ever

“Photographed a class of 1 and 2 year olds (I mostly did preschool.) Their teacher had written herself thank you notes as if they were coming from the pre-verbal children. Like ‘Dear Ms. Judy, thank you for changing my diaper.’ ‘Dear Ms. Judy, thank you for giving me snacks every day.’ She had written one for every kid, and hung them up all over her wall. Later as I was trying to navigate my tripod through a hallway, she felt I was in her way and threatened to bash my face in with a door” (Source).
It’s My Real Hair, Honest!

“Kid I went to high school with showed up on picture day wearing a giant afro wig. He had worn a wig the year before but it wasn’t as noticeable so our Senior year he decided to push it. These weren’t yearbook shots just school ids. He gets to the front of the line and the photographer tells him to take the wig off. He argues it was he real hair and even breaks out the my dad is black argument. Finally the guy just lets him take the picture with the wig on” (Source).
Where Do I Start?

“I asked a 4th grader if she hurt her foot. ‘Uh, I have a prosthetic leg’. She was wearing sandals and sure enough rubber foot.
I asked a 7th grader to sit up straight, spinal problems. His doctor bought a copy of the photo as a before shot for a textbook he was writing. Whatever the doctor did, it worked like a charm. A kid told my assistant that they ate their pet rabbit the night before.
I asked a kid to sit down. He sat down on the floor. I told him, ‘Not on the floor, on the chair. Please point your knees at the computer.’ He got up and touched his knee to the computer. I said, ‘No, sit on the chair and turn your knees point them at the computer.’ I asked a kid if they wanted their hoodie to be in the picture. ‘No’. Ok, take your hoodie off. ‘No’. Do you want your hoodie in the picture? ‘No’. If you don’t want your hoodie to be in the picture, you have to take it off or it will be in the picture. ‘Oh, I want my hoodie in the picture.’ I tapped a kid on the shoulder from behind and asked where the teacher was. She was the teacher, and I had known her for almost 20 years by that point. Asked a teacher if a severely disabled student could sit by themselves on the bench. The student couldn’t and there was a pretty hard thump on the gym floor” (Source).
I’m Not a Superstar

“When I was 16, I was recovering from a serious illness that left me partially blind and very sensitive to light, so I wore those big old-lady cataract sunglasses all the time. Picture day, sat down for my photo, and the photographer says ‘How about you take off those glasses superstar? You don’t look cool.’ I said ‘I can’t, I need them’ and he replied ‘You don’t need them, you just think you look good in those.’ My soccer coach came over and let him know exactly where he went wrong while I sat in the photo chair trying not to cry” (Source).
Wolverine Is My Secret Identity

“A kid handed me the little card with his name on it. Let’s call him Dave. I took it and read the card and said ‘Hi, Dave!’ He said, ‘I’m not Dave. My name is Logan.’ I said, ‘Oh no, I must have the wrong card… I’ll look for the one that says Logan.’ Then he exclaimed, ‘I’m Wolverine!'” (Source).
Photography Can Be Dangerous Business

“As I said in the other comment, we work in teams typically. We do lots of shoots together, and my best friend and I have actually been in the business a while. We’ve had a lot of third partners; they generally come and go thinking this was their ‘passion’ then realizing they’d rather do something like Instagram or whatever. One of our first third partners was a guy we’ll call Rick who was a bit of a d–k, but he did the job well and got the job done. In our very first shoot, Rick got the typical crying kid who slobbered all over him to try not to get the picture taken, so we had a bit of empathy for him, but that changed after the incident. Basically we were doing a shoot for a high school, and there was a girl (among dozens) with big breasts and a low cut shirt. I’m not sure how she was posing, because again I wasn’t there, but we generally don’t touch high school students when helping them pose since usually they get what we mean when we say ’tilt your head this way’ or ‘sit up straight.’ Well Rick almost immediately began touching this poor girl. Which seems creepy all on its own. Apparently the girl was one of the school’s ‘special needs’ students (I don’t know the PC term nowadays), and when Rick ‘accidentally’ gently brushed against her bra while helping her sit straight, she screamed and hit his d–k. That’s the perspective of the students. My perspective was taking a picture of a dude who was so ripped that I was feeling emasculated, hearing the screaming of a girl, the screaming of another girl (who turned out to be Rick), running over, and seeing him bent over grabbing his crotch while she is sobbing. Apparently it all happened very fast but we never worked with him after that. I’m not sure what if any criminal complaints were made against him about that particular case, but more strange things followed.
We also found weird footage from his cameras after the fact, but I’m not sure that’s totally relevant? Unless I’ve dug myself in too deep already? Basically, Rick touched a special girl and got a special punch” (Source).
Only Do One Arm, Please

“The photographer who did my senior photos told me the weirdest request she had gotten so far that year was a girl who very specifically wanted just one arm photoshopped to be especially thin. It ended up being a girl in my class and I noticed the second I saw her picture in the yearbook. She was a bigger girl so she had one chubby arm and one very, very, very skinny twig-like arm. She didn’t seem to notice how weird it was. She was one of the more popular girls so of course everyone looked at her picture and noticed. She had no clue. She only focused on the arm that was closer to the camera. I was torn between feeling bad and wanting to laugh hysterically. I chose both” (Source).
Santa, Is That Really You?

“I do Santa photography. Had a 12 year old boy come in with his family. He was extremely excited to meet Santa. So excited, he decided to pee his pants as I was setting the shot up. Didn’t see until I took the first photo. With some clever hand positioning I was able to hide it for the most part. Parents didn’t even notice” (Source).
I Think We’ve Got All the Shots We Need

“I’ll try to remember some stories later but there was one shoot I’ll never forget. First off, we were expected to do 3 sets of pictures for each student, one for the yearbook (tux for boys, drape for girls) one for cap and gown and one set of casuals. Casuals usually involved hand poses with a table we’d bring and some cutesy stuff, like holding a rose up to your shoulder, or like full body pictures meant to show off their clothes. So a girl comes in, she looks OUT of it. Like really not connected to the world. I take the yearbook pics, I take the cap and gown. All the while her smiles are so obviously faked and her eyes are just gone. It’s okay, I was used to dealing with students who didn’t want their picture taken. I’m pretty good at loosening them up and making them laugh, but she was barely paying attention to me. She seemed really distracted. I tell her to change into her regular clothes to take her casuals and she’s like ‘okay’ all monotone. She comes back and has huge bandages on her arms. Clearly this poor girl had tried to kill herself rather recently and was just taking these pictures out of obligation or something. Every casual photo I’d take of her would have those bandages and there would be no mistaking why they were there. Instead of taking them and having them show up in the proofs that would go out to the parents, I tell her, ‘okay you’re good, thanks for coming!’ And she just shrugs and leaves, just as apathetic as before. This was like 6 years ago and I still think about her sometimes and I hope she’s happy now” (Source).
No, I Will Not Date You

“Being a young female photographer, probably having to photograph male, high school seniors is the most awkward. I’ve been asked out on dates, hit on, winked at, and straight up had any and all requests for them to smile nicely, stop goofing around or take their hat off ignored” (Source).
Are You Sure We Shouldn’t Retake That?

“I am not a photographer, but my senior year in high school I almost ended up with my boyfriend’s picture above my name in the yearbook instead of my own. We had to go in for pictures about a week before school started at a specific time depending on last name. So ‘A’ names went at 10, ‘B’ names at 10:30, and so on. My last name and my boyfriend’s started with the same letter. We lined up together, and the lady gave us our barcode cards with our names. I got my picture taken, and then waited just outside the picture area for my boyfriend. I watched as the photographer neglected to scan my boyfriend’s card, took the picture (overwriting my picture), realized the mistake, scanned the correct card, and took the picture again. I asked him if I needed to do my picture again but he waved me away. A few weeks after school starts, we got our ID cards. Well, everyone but me. One of my friends was an office aide, and he was cracking up every time he looked at me at lunch. When asked why, he said ‘you’ll see.’ I was called to the office and shown my ID card, which had my boyfriend’s picture on it. They wouldn’t let me just take it, and said I had to do picture retakes.
Throughout the year, the picture of my boyfriend was associated with my name in the school’s computer system. I got a lot of double takes from new teachers who would look at the name and picture when calling roll, and then see me and be confused. Somehow my retake picture ended up on my ID but nowhere else. The yearbook only ended up with my correct picture because I had a friend on yearbook staff who caught the mistake before it went to print. The picture company did send me free copies of both my pictures and the ones of my boyfriend though, which was nice. Basically, the photographer accidentally overwrote my picture with a picture of my boyfriend, picture of boyfriend followed me around all through senior year” (Source).
Delete Them All

“Wow, something I can answer for once. About 6 months ago I had to do a shoot for an all boys school. The day went as normal, majority good shots, a few clowns but ‘ya know that’s what I come to expect. But something happened that I will never forget.
A kid comes out, and I have no clue what’s wrong with him, he seems really nervous. I take a few shots and he seems really disengaged. On my final shot he starts scratching his arm rapidly. Then he yelled at me. ‘Delete the photos!’ At this point I don’t know what to say…I pretty much say that I’ll go and talk to my superior and walk away. My supervisor said I could, so I did.
I came back to the kid and I told him I deleted the photos. He says that he doesn’t believe me and stands up. I showed him my camera and he freaked out and threw my camera to the ground, somehow breaking it. This child then proceeded to run off…
My cannon 700D was broken, by some mentally troubled child…that’s my story” (Source).
These Samurai Swords Definitely Look Cool

“I did senior portraits and this really nerdy lookin kid wanted photos with his two samurai swords. I tried my best to make it look cool but… I just… couldn’t. Another senior did couples photos with her boyfriend. They specifically earnestly requested a pose where the girl posed all cute on one side of the couch, while the boy sat on the other side of the couch, staring at her while stroking his beard. That one didn’t turn out well either” (Source).
You Should Know That Already

“Can we do funny? When I was a school photographer, to amuse myself I tried to give each kid in class a unique word to say. ‘Fuzzy puppies!’ ‘Funky monkeys!’ Etc etc. So I get this little girl at my chair. She’s got the thickest glasses I’ve seen, an overbite, and is pale as a vampire. But whatever. A kid is a kid. So I say, ‘Okay, say Fuzzy Kitties!’ And she gives me the most irritated look I’ve ever seen. ‘Uh, I’n allergic to kitties.’ Like it was the dumbest thing anyone had ever said to her, and she felt sorry for how dumb I was” (Source).
I’m Totally Ready for College

“Probably the most awkward moment I had was working with Lifetouch and photographing a girls senior portrait when I was 23. She went on and on about how she was 16 and skipped a grade because she was so smart, I told her that was good for her but could be hard when it came to college. She responded with a story of her spring break in Mexico where she did a wet T shirt contest and was in the top 3 contestants. Most awkward conversation I’ve ever had doing senior portraits” (Source).
A Sad Turn of Events

“My mom was a school photographer, mostly for elementary schools, when I was younger. The day after Halloween [maybe a few days after?], she went to a school in a nearby city that was known for having a kind of like, haunted Halloween mine shaft tour because it used to be a mining town. Something went wrong on the tour that Halloween, and one of the tour guides was killed in the middle of the tour, in front of the whole group. I think she was pulled out of the cart and run over, or partially decapitated – I forget exactly. But she died, pretty gruesomely. And people thought it was a Halloween prank and part of the tour, so nobody stopped to help her right away. It was a f–ked up situation. Her kids went to that school. And they were there for picture day. My mom said it was so tragic because they looked completely devastated and had clearly been crying like crazy [of course] and nobody could really understand why they were back at school so soon. That’s the story I remember the best” (Source).
That’s a Very Busy Portrait Session

“There was a very small country mountain high school we used to take senior pictures at every year. Only about 15 or 20 seniors each year, but there was no other photo studio or services for a few hours drive, so when we came to town to take pictures, it was a big deal. I did several sessions where I was taking entire family photos, newborn baby pictures, and bridal portraits during their senior portrait sessions. Yes, bridal portraits. Some were for upcoming weddings, but most were for the wedding (and/or children) they had already had during their junior year that they had no other pictures for” (Source).
We’ll Just Have You Stand Up

“Definitely the girl whose skirt was so tight and small that she couldn’t hide her panties when she was on the stool. I wasn’t the one photographing her (three of us do photos at once during orientations), but I heard the commotion and walked over and could not believe it. She ended up getting her photo taken standing. Honorary mentions: Every dude ever with an obvious random boner. Maybe you got your first hug since before summer? Either way, the camera doesn’t see it. Rock on. The girls who try to do duckface are all cringe worthy. I don’t have a particular story, but you’re welcome in five years when you go back to your yearbook and you don’t look like an aquatic bird. To everyone who claims to not know how to smile, you’re generally great. To the girl whose smile made me laugh out loud because it was so forced, I’m sorry. I get not everybody is photogenic. But you should have seen your face.
I also have a creepy-ish story if anybody wants to hear…” (Source).
He’s Not Getting a Date Out Of It.

“I once photographed a special needs school, and I thought it went very well. I took my time, I was patient, I think I got some shots that the parents probably didn’t often see. The director was also impressed. Next day he called the office that scheduled me to see if they could help him get in touch with me for a date. Awkward. Here’s more info. People are assuming I turned him down because he was ugly. He wasn’t ugly. I was in a relationship already, but it doesn’t matter. I think most women, regardless of attractiveness or relationship status, would not like to be approached in this way. I think guys are being genuine in wanting to know why it’s a little off putting, so I will try my best to explain. Here’s the thing about school photography: you’re in a new place almost every day. You interact with people for a day or two, and move on. There’s acting involved to a degree, you act super cheerful and friendly regardless of how bad things are in your life, how much pain you are in, how exhausted you are. You smile all day to bring smiles to everyone else. But it’s shallow. It’s not entirely real, or reflective of the rest of a person’s life, their passion and interests. I was everybody’s Single Serving Friend. The directors are something in between a client and my boss for a day, so I agree with the person who says there’s a bit of an imbalance of power. I have to pretty much do what they say, in work related things. They are also responsible for giving me ratings about how I performed that day, and that directly affects any pay raises. So I’m a little skeptical of someone feeling like we had a connection based on that. It’s a little like thinking your Starbuck’s barista is flirting with you, because she’s required to serve you with a smile. Asking other coworkers for that barista’s number puts everyone in a weird position. But if someone did want to take a chance and asked me out based on what they see from my work, here’s what I’d personally prefer. He could say something like ‘Hey, it was great working with you today, and I’m impressed with how well you do with the children. This makes me think you’re probably a good person. I’d like to see you outside of work if you are open to it. Here’s MY number if you are interested. If you’re not, it’s ok, and I’ll tell your office that you did an amazing job regardless of your answer.’ That would have been a lot less unsettling to me. I can’t speak for everyone else” (Source).
Just Ignore Your Mother

“I’ve done all grades from kindergarten to university so I have a few. Photographing a child who was in grade one and trying to get them to look/smile while the mother is standing five feet to the left of me yelling at her kid to stop looking at her and look at the photographer but being really loud and obnoxious so the child obviously looks at her. I finally get the mother to stop and take a nice photo only for her to look at it and say it’s an ugly smile. That poor child looked so crushed…” (Source).
That’s Not a Girl

“While setting up a class of grade 3 kids for their class photo shoot, I asked one girl who was wearing a complete pink outfit and Disney princess light up shoes and very long and luxurious hair to take a seat on the end of the bench, the kid nodded and took a seat. So I asked the next kid in line to sit next to the girl in pink, but the ENTIRE class yells and points to the kid saying ‘THATS A BOY NOT A GIRL!! HA HA! SHE CALLED YOU A GIRL!!’ I was mortified and apologized. The kid cried but surely I couldn’t have been the first person to call them a girl. The school photography game has lots of interesting stories. I could write a book” (Source).