"When I was in pre-k, my dad was the one who dressed as Santa for our class. Apparently, little 3 year-old me climbed onto his lap, and said 'Hey, you stole my dad's watch!' and got really upset."
"Did Santa for a foster/adoption ministry. You have to get special background checks/training to watch foster kids in Texas, so it's really hard for foster parents to find time to Christmas shop sans kids. This ministry does the training and checks on people like me and several of us get together once a quarter or so for a date night/need to get things done night for these parents.
Anyway, I dressed as Santa while mommy and daddy had a date night and got Christmas shopping done. There were probably 300 kids there and they all got to come take pictures with me/tell me what they wanted. Great fun, until... one of them asked me for a mommy and daddy. He couldn't have been 3 and he said it with a straight face. I won't lie...Santa cried a little that day.
For those who need resolution, he was adopted by the parents who were caring for him at the time."
"Wow, up my alley. I was a manager of one of theses place for 5 years or so, and occasionally filled in as santa when someone was late or sick. The 3 most messed up things I was asked for were:
Mommy to live until Christmas (cancer). I was shocked and don't even remember my response. It's all I thought about until that Christmas.
Mommy and daddy to stop yelling at each other. I asked the kid to go see one of my helpers, then I talked to the parents. The dad got all quiet and the mom teared up, it was like they never noticed the kid noticing them. They kinda nodded and walked away with their heads down.
A certain adult toy. This happened a few times, usually it was an older girl trying to be dirty, or a group trying to be funny, but this one girl was about 12 or 13 and seriously just wanted that. She didn't even giggle or smile suggesting that it was a joke.
I have lots more. Sadly only the really messed up stuff sticks because some of the really silly stuff is so out there it gets old hearing about a kid what wants a 5th pony."
"I didn't have much of a concept of Santa as a child. My parents hadn't really bothered with the story, by age 6 I knew of him but my parents were like "he's just a made-up, like a cartoon character, to help tell stories." But before that, I hadn't really been prepped with any Santa mythology.
When I was four or so, we went to a Christmas party at my Dad's work and Santa tried to pick me up and sit me on his knee. I started screaming and crying and kicked him repeatedly and then hid under the Christmas tree trembling until my big brother got me out. Later "Santa" came to apologize and I told him it was not okay for strangers to touch children. My mother tells this story with some pride."
"Our colleague just died of brain cancer. Prior to his passing (the Christmas before) our other coworker (who dresses semi-pro as Santa) asked his daughter age 8ish, she said she wanted a cure for brain cancer. Santa lost it."
"So I was working as a shopping center in Leicester (England) as one of Santa's helpers (2012), anyway it was my job to sit behind the chair and write down what all of the kids wanted (the shops buy the statistics), anyway basically every kid (at least 90%) wanted some form of smartphone, Ipod, Ipad etc... the other 10% asked for generic stuff (Lego barbies toy cars etc.....) until there was this one kid turned up buy himself (looked about 11-12) that looked really strange but I couldn't put my finger on what other than that he was a larger child and had a strong Scottish accent. Anyway he sat on Santa's lap at witch point Santa winced (this kid looked quite heavy) so he was asked ''what do you want?'' so he leaned in really close to Santa (I had to re-position myself to hear) then he blurted ''about tree fiddy."It was then that we realized that he was the lock ness monster and he had fooled us again. After that we just stared at each other and he just slithered away."
"I dressed as Santa for my son's 1st grade class this year. The kids figured out who I was fairly quickly, but that didn't stop them from taking turns telling me what they wanted. One little kid asked me if he could have his sister back. Teacher later explained that there was a very bitter custody battle and one parent took their favorite child of the two and had moved to another state."
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"Kid asked for Santa to kill his friend. He was like seven. All he did was not share his power ranger toy."
"Not really messed up, but a memorable moment from the time I got to be the fat man in red.
I don't exactly have the build to be Santa, but I was the only one who didn't outright object to putting on the suit at the ice rink where I worked. I had to wear it during the public skate times and basically interact with the kids for a Skate with Santa! promotion.
A lot of the middle school boys chased me around and asked me questions like, "Where's your sleigh?" and "I saw you at the mall earlier today, how did you get here so fast?" and "Can I pull on your beard?" This went on for an hour, it was pretty annoying that it seemed like nobody was actually happy to see me, but I didn't blame them - I hardly looked like the Santa Claus anyone would typically imagine. I started watching the clock, anticipating when I could finally rip off the suit. I saw why no one wanted to volunteer.
About 15 minutes left, a dad comes up to me and asks if his little girl could talk to me. She's about 5, dressed in pink from head to toe (including skates), long blonde wavy hair, big blue eyes. I say sure, get down on a knee, and wave her over. She leans in and whispers in the daintiest little voice I've ever heard, "Hi Santa. Um, I want a Barbie, and a DS, and, um, I want my dad to give me a big hug on Christmas."
It was amazing - this little girl brought me to a place I hadn't been to in almost 20 years. For that fleeting moment, this little girl made Santa real again, and I can't even describe the warmth and joy I felt because of that moment we shared."
"When I was in grade school I had a friend named Stacy who came over to play frequently since we lived in the same neighborhood. Stacy had a sister maybe 8 or 10 years older who'd come over to play a lot too, because she had Down's Syndrome and was still into Barbies and Mall Madness and stuff. But because we were kids and she was different and we were cruel, we didn't always want Stacy's sister to play with us, so when she'd come over she'd actually end up spending a lot of time with my dad, who let her help make dinner. So unsurprisingly Stacy's sister developed a huge crush on my dad, and hated my mom. When Christmas came around Stacy's sister told Santa she wanted my mom to die."
"When I was 4 I asked a mall Santa for a globe. He turned and gave my mom a "Lady, what the f--- is with this kid" look."
"I walked by a Walmart Santa and I heard the kid in his lap ask for a gun. I stopped to listen. When Santa asked why, the kid said, "because I want to kill bad guys like the guys on daddy's games!" This kid obviously watched his dad play call of duty."
"When I was in high school I remember going to the mall around Christmas time. The fake Santa was really close to the Mrs. Fields. A kid asked for a giant Mrs. Field's cookie, his mother shook her head no at the Santa, so the Santa suggested he ask for something else. The kid started screaming for the cookie at the top of his lungs. After about 2 minutes of this the kid threw up all over the Santa and fell asleep. Turns out he had just eaten 3 smaller cookies from Mrs. Fields."
"I have done Santa for Big Brother Big Sister's for 7 years. Almost every year one of the kids gets me in the crys. The first one was a little boy. When I asked him what he wanted he said, "I don't want anything for me I just want a family for my sister." WOW got me what the hell do I say to that. Next one a little girl asked me to make sure her daddy got back from Afghanistan alive....I was speechless and didn't know what to say. It is the best day and the worst day of the year when I am Santa."
"I asked for a Chucky doll when I was 4. My Mum didn't know why people were giving her funny looks in the toy stores until she got home one day to see me watching my desired doll on VHS. Brothers were in trouble. Still waiting for my Chucky doll."
"I'm not a fake Santa, but when I was five I went to a Christmas party with my mom but she told me my dad couldn't make it. I sat on the fake Santa's lap and wished that my dad could be at the party. Half an hour later my dad appeared. I found out a few years later that he was the fake Santa."
"I was a Santa at a school on the near an Native American Reservation and the top 4 most messed up and sad things I heard was. 4. A new puppy because ours froze and he is not coming back 3. I wish my parents would stop fighting 2. I wish to see my Mommy/Daddy or to come home 1.I wish my Dad/Mom/Uncle/Brother to stop drinking.
Hard times to look into a childs' face and in your heart know there is not much you can do but they have a look of hope that you might be able to help them. I only did it for 2 years and I stopped volunteering."
"My mother still keeps one of the letters I wrote to Santa back then, asking for a golf set, including holes! I think its funny."
"Not so much messed up as it is sad. A 6 year old girl asked me (as Santa) for a friend. How depressing."