Rich Man Met an 8-Year-Old Boy in the Town Square on Christmas Eve — ‘Can You Help Me Find My Family?’ the Boy Asked

On Christmas Eve, a wealthy but lonely Dennis stumbles upon a lost eight-year-old boy in the town square. Haunted by memories of his own childhood, Dennis soon finds his life changing in ways he never expected.

The square was alive with lights and laughter. Kids zipped around on skates, their cheeks red from the cold. Couples walked hand in hand, leaning close, bundled up, and smiling. A small group of carolers sang on the corner near the big tree, voices warm even in the chilly air.

A snowy street on Christmas | Source: Pexels

A snowy street on Christmas | Source: Pexels

I took it all in, trying to feel… something. You’d think a successful guy like me, an orphan who grew up to be a businessman, wouldn’t feel out of place here.

But here I was, alone, like every other holiday season. I’d had a few relationships over the years, but my partners saw dollar signs, not me.

A sad man outside on a snowy day | Source: Midjourney

A sad man outside on a snowy day | Source: Midjourney

Suddenly, I felt someone collide with me, and I turned to see a young woman sprawled on the ground, looking up at me with a grin. Her laughter was contagious, and for a split second, I couldn’t help but smile back. She was beautiful, bright-eyed, with a spark that caught me off guard.

“Oops,” she laughed, still sitting there. “Sorry! Guess I’m not as good on skates as I thought.”

A woman on a skating rink | Source: Midjourney

A woman on a skating rink | Source: Midjourney

“It’s alright,” I said, offering a hand to help her up. “You sure you’re okay?”

But just as quickly, a tall guy came over, scowling as he pulled her away from me. “Hey, buddy, what’s the deal here? Hitting on my girl?”

“No, I wasn’t,” I said quickly, backing off, with my hands up. “Just helping her up, that’s all.”

An aggressive man on a skating rink | Source: Midjourney

An aggressive man on a skating rink | Source: Midjourney

“Yeah, well, don’t,” he muttered, shooting me a glare as he led her away. She looked back once, mouthing a quick “Sorry,” and then they were gone, swallowed by the crowd.

I stood there for a moment, shaking my head. “So much for miracles,” I muttered. I turned to leave, ready to head home.

An upset man on a skating rink | Source: Midjourney

An upset man on a skating rink | Source: Midjourney

Then I felt a small tug on my coat. I turned around, half-expecting that girl again, but instead, I found myself looking down at a boy. He couldn’t have been more than eight, with wide brown eyes and a nervous look on his face. He clutched a small keychain, his hand trembling.

“Excuse me, sir,” he said, voice soft and polite. “I… I need some help. I can’t find my family. Haven’t seen them in days.”

A sad boy next to a Christmas tree | Source: Midjourney

A sad boy next to a Christmas tree | Source: Midjourney

The words hit me like a blast of cold air. “You… you lost your family?” I asked, lowering myself to his eye level. “When did you last see them?”

The boy looked down, shuffling his feet. “I’m not sure. I been lookin’ for a while, though. But… but please, sir, don’t call the police.”

“Not the police?” I asked, puzzled. “But if you’ve been lost for days—”

A serious man talking to a boy | Source: Midjourney

A serious man talking to a boy | Source: Midjourney

He shook his head vigorously. “No, no police. I heard people sayin’ that sometimes, when parents don’t have much money, the police take kids away. And… and my family doesn’t have much. They’re poor. I’m afraid they’ll… well, they’ll take me away, too.”

I looked at him, feeling a pang of something I hadn’t felt in years. I knew what it was like to be a kid worried about getting taken away.

A sad boy in an orphanage | Source: Midjourney

A sad boy in an orphanage | Source: Midjourney

“Alright,” I said gently, resting a hand on his shoulder. “No police, I promise. We’ll just… we’ll figure this out. Okay?”

He nodded, relief flashing across his face. “Thank you, sir. I didn’t know who else to ask.”

“Call me Dennis,” I said. “And what’s your name?”

A smiling man talking to a young boy | Source: Midjourney

A smiling man talking to a young boy | Source: Midjourney

“Ben,” he replied, clutching his keychain a little tighter.

“Alright, Ben,” I said. “Let’s get you home. Do you know where you live?”

He nodded. “It’s a little ways from here. I can show you. I think I remember.”

A sad blue-eyed boy | Source: Midjourney

A sad blue-eyed boy | Source: Midjourney

I called my driver, and we waited in the cold as he pulled up to the curb. Ben climbed in first, tucking himself into the back seat. I followed, shutting the door and glancing over at him. “So,” I said, trying to make conversation, “what kind of keychain is that? Looks pretty special.”

He looked down, fingers wrapped around the tiny silver heart on his keychain. “It’s… well, it’s just a keychain they give you at this place I stayed at once.”

A small silver keychain | Source: Midjourney

A small silver keychain | Source: Midjourney

I looked at it more closely, realizing that it looked familiar. Very familiar.

“So, you like Christmas?” I asked instead.

“Yeah, it’s nice,” he mumbled, still looking out the window.

When we reached the address he’d given, I got out and walked with him up to the front door. He knocked once, then again. Silence.

A sad boy near a door | Source: Midjourney

A sad boy near a door | Source: Midjourney

“Maybe they went to my grandparents’ place,” he said, though he didn’t sound convinced.

I glanced back at the square, its lights twinkling in the distance. “Alright, Ben,” I said, kneeling down to his level. “Maybe we’ll give it some time. How about we head back to the square and enjoy a few things while we wait? Have you ever been skating?”

A smiling man looking down | Source: Midjourney

A smiling man looking down | Source: Midjourney

He looked at me, his eyes lighting up. “I haven’t! Can we?”

I stood up, smiling. “Sure. Why not?”

As we headed back to the square, Ben’s face lit up with excitement. The whole place was glowing, with lights strung up on every tree and children darting around. I hadn’t done much for the holidays in a long time, but tonight felt different.

Christmas fair | Source: Pexels

Christmas fair | Source: Pexels

“So, skating first?” I asked, nodding toward the rink.

Ben’s eyes went wide. “Really? Can I?”

“Absolutely. Let’s get some skates.”

A boy on a skating rink | Source: Freepik

A boy on a skating rink | Source: Freepik

Minutes later, we were on the ice. Ben took off, shaky at first, his little arms flailing. I was no expert, but I managed to stay upright. We slipped, stumbled, and laughed. I felt lighter than I had in years.

“Look, Dennis! I got it!” he shouted, gliding a little more steadily, a grin stretched across his face.

A man smiling after he fell on a skating rink | Source: Midjourney

A man smiling after he fell on a skating rink | Source: Midjourney

“You’re a pro already,” I laughed, half-joking. “I’m gonna need lessons from you!”

After skating, we tried one of the carnival games—throwing rings onto bottles. He didn’t win, but he nearly knocked over the whole stand with how excited he was.

“Can we get hot chocolate?” he asked, eyeing the stand nearby.

Hot chocolate | Source: Pexels

Hot chocolate | Source: Pexels

“Of course,” I said. We got our steaming cups, finding a bench to sit and watch the crowd. As he sipped, Ben looked so content. His cheeks were flushed, and there was a peace in his expression that felt like a gift.

I looked at him, a warmth growing in my chest that I hadn’t felt in years. I’d only known this boy for a few hours, yet I felt connected to him. And I didn’t want the night to end.

A happy boy holding hot chocolate | Source: Midjourney

A happy boy holding hot chocolate | Source: Midjourney

But eventually, I cleared my throat. “Ben, maybe… maybe it’s time to head back to the shelter.”

He looked up, surprised, and for a moment, his face fell. “How did you know?”

I smiled gently, pointing at his keychain. “I recognized that keychain the second I saw it. They gave out the same ones when I stayed there.”

A man talking to a boy on a Christmas fair | Source: Midjourney

A man talking to a boy on a Christmas fair | Source: Midjourney

His eyes widened. “You… you were at the shelter?”

I nodded. “A long time ago. I was around your age. So, I understand. I get what it feels like to want a family, even just for a night.”

Ben’s eyes dropped to the ground, and he nodded slowly. “I just… I wanted to feel like I had a family, you know? Just for Christmas.”

An upset boy | Source: Freepik

An upset boy | Source: Freepik

“Yeah,” I said softly. “I know. And I’m really glad I got to spend Christmas Eve with you, Ben.”

He looked up, and I saw the gratitude in his eyes. “Me too, Dennis.”

We walked back to the shelter in silence, the warmth of the evening settling between us. When we arrived, a familiar face was waiting outside. It was her, the young woman who’d bumped into me earlier. Her eyes widened with relief as she spotted us.

A concerned woman sitting on a street | Source: Midjourney

A concerned woman sitting on a street | Source: Midjourney

“There you are!” she exclaimed, rushing over to Ben and hugging him tightly. “We were so worried about you. We should notify the police you’re back.”

Ben squeezed her hand, mumbling, “I was okay. Dennis helped me.”

The woman looked up at me, her expression softening. “Thank you so much for bringing him back.” She let out a breath, then added with a tired smile, “I’m Sarah. I volunteer here. We’ve been searching for him since this afternoon.”

A smiling man talking to a woman | Source: Midjourney

A smiling man talking to a woman | Source: Midjourney

“Nice to meet you, Sarah,” I said, realizing this must be more than a chance meeting. We stood there for a moment, caught in a quiet, shared relief. She looked exhausted, her face a mix of worry and something else—hurt, maybe.

I hesitated, then asked, “Rough night?”

A man talking to a woman on a Christmas fair | Source: Midjourney

A man talking to a woman on a Christmas fair | Source: Midjourney

She nodded, looking away. “I found out my boyfriend… well, he was cheating on me. Tonight, of all nights.” She laughed sadly, brushing a tear away. “But I guess that’s how it goes.”

On impulse, I blurted, “Well… would you maybe like to get a coffee?”

She looked down at Ben, then back at me. “Actually… I’d love that.”

A smiling woman outside | Source: Midjourney

A smiling woman outside | Source: Midjourney

Over the next few months, I found myself at the shelter often. Sarah and I would meet there, talking for hours and helping out together.

The more time we spent, the closer we grew, both to each other and to Ben. He seemed to shine whenever we were all together, and soon the shelter felt like the home I hadn’t realized I’d been missing.

A happy family on a walk | Source: Midjourney

A happy family on a walk | Source: Midjourney

By the time the next Christmas rolled around, everything had changed. Sarah and I were now married, and Ben had officially become our son. That Christmas Eve, we went back to the square, the three of us hand in hand, surrounded by laughter and lights.

We watched the skaters, sipped our hot cocoa, and felt at peace as our own little family, a miracle in the making.

A happy family together | Source: Midjourney

A happy family together | Source: Midjourney

Liked this story? Consider checking out this one: When Sutton is on a business trip, the last thing she expects to discover is that her husband is having an affair, resulting in a pregnancy. But after Jacob moves out, and the months go by, Sutton plans her revenge.

This work is inspired by real events and people, but it has been fictionalized for creative purposes. Names, characters, and details have been changed to protect privacy and enhance the narrative. Any resemblance to actual persons, living or dead, or actual events is purely coincidental and not intended by the author.

The author and publisher make no claims to the accuracy of events or the portrayal of characters and are not liable for any misinterpretation. This story is provided “as is,” and any opinions expressed are those of the characters and do not reflect the views of the author or publisher.

I Told My Date about My Specific 3-Year-Rule, but He Immediately Left and Blocked Me – Is It Really That Weird?

Addison’s life revolves around her demanding job as a neurologist, leaving little time for romance. When her cheerful coworker Nathan sets her up on a blind date with a seemingly perfect guy named Jake, she finally feels a spark of hope. However, after Addison shares her three-year dating rule, her date abruptly leaves. What went wrong?

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I always thought my life would stay the same.

Day in and day out, the hospital consumed all my time.

A smiling young doctor | Source: Midjourney

A smiling young doctor | Source: Midjourney

My name is Addison, and I work as a neurologist. My days are filled with patients, charts, and endless rounds.

It’s a fulfilling job, but it leaves little room for anything else, especially dating.

A busy young woman | Source: Midjourney

A busy young woman | Source: Midjourney

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One day, while grabbing a quick coffee in the break room, my coworker Nathan walked in with a bright smile on his face.

Nathan is always in a good mood, no matter how stressful the day gets.

A smiling doctor | Source: Midjourney

A smiling doctor | Source: Midjourney

“Hey, Addison,” Nathan said, leaning against the counter. “How do you feel about blind dates?”

I laughed, almost spilling my coffee. “Blind dates? Nathan, you know my schedule. I barely have time to eat, let alone date.”

Two professionals laughing and chatting | Source: Midjourney

Two professionals laughing and chatting | Source: Midjourney

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Nathan chuckled. “I know, but hear me out. My friend Jake is a great guy. He’s kind, funny, and I think you two would hit it off. What do you say?”

I paused, considering it. I hadn’t been on a date in ages, and the idea of meeting someone new was intriguing. Plus, Nathan seemed genuinely excited about it.

A couple enjoying drinks | Source: Pexels

A couple enjoying drinks | Source: Pexels

“Okay, then,” I said, smiling. “You’ve convinced me. When’s this magical date happening?”

Nathan’s face lit up. “Really?? How about next Tuesday night? It’s the only evening that works for both of you!”

A doctor with his arms crossed | Source: Midjourney

A doctor with his arms crossed | Source: Midjourney

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Next Tuesday. I mentally checked my calendar. It was one of the rare nights I didn’t have a late shift or any other commitments.

“Next Tuesday works for me,” I said. “Let’s do it.”

A female doctor talking to a male doctor | Source: Midjourney

A female doctor talking to a male doctor | Source: Midjourney

Nathan grinned. “Great! I’ll set it up and text you the details. You won’t regret this, Addison,” he said with a wink.

“We’ll see that,” I laughed and finished my coffee quickly.

A smiling doctor | Source: Midjourney

A smiling doctor | Source: Midjourney

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As I walked back to my office, I felt both excited and nervous. It had been so long since I had gone on a date.

My life had become a routine of work and more work, with little time for anything else. But maybe this was what I needed — a chance to step out of my comfort zone.

A doctor lost in her work | Source: Midjourney

A doctor lost in her work | Source: Midjourney

The rest of the day flew by in a blur of patient consultations and medical charts. But in the back of my mind, I kept thinking about the upcoming date. Maybe, just maybe, this blind date with Jake would be the start of something new.

On Tuesday night, I arrived at the quaint restaurant Nathan had suggested.

Inside a restaurant | Source: Freepik

Inside a restaurant | Source: Freepik

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It was cozy, with dim lighting and a warm ambiance that immediately put me at ease. As I walked in, I spotted a man sitting at a table near the window.

He looked up, smiled, and waved me over.

This must be Jake, I thought to myself.

A smiling man at a table | Source: Midjourney

A smiling man at a table | Source: Midjourney

“Addison?” he asked as I approached the table.

“Yes, and you must be Jake,” I replied with a smile.

A couple on a date | Source: Freepik

A couple on a date | Source: Freepik

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We shook hands, and I took a seat. Almost immediately, the waitress came over to take our drink orders.

“I’ll have a glass of red wine, please,” I said.

“I’ll have the same,” Jake added.

Two people enjoying wine | Source: Freepik

Two people enjoying wine | Source: Freepik

As the waitress left, we started chatting. Jake was easy to talk to, and I felt my initial nervousness melt away.

“So, Nathan tells me you’re a neurologist,” he said, looking genuinely interested. “That must be a challenging job.”

A couple lost in each other's eyes | Source: Freepik

A couple lost in each other’s eyes | Source: Freepik

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“It is,” I nodded. “But I love it. What about you? What do you do?”

“I’m a graphic designer,” Jake replied. “I work freelance, so my schedule is pretty flexible. It’s a lot of fun, especially when I get to work on creative projects.”

A person working on their laptop | Source: Pexels

A person working on their laptop | Source: Pexels

Our drinks arrived, and we ordered appetizers — stuffed mushrooms and bruschetta. As we nibbled on the delicious food, we continued to talk about our lives, hobbies, and interests.

“I love hiking and photography,” Jake said, taking a sip of his wine. “There’s something about being in nature that’s so refreshing.”

A male photographer | Source: Pexels

A male photographer | Source: Pexels

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“I’ve always wanted to get into photography,” I said. “But I never seem to find the time. Maybe you could give me some tips?”

“I’d love to,” Jake said with a smile. “It’s all about finding the right light and angle.”

A woman with a camera | Source: Pexels

A woman with a camera | Source: Pexels

As the evening went on, I found myself more and more charmed by Jake. He was kind, funny, and easy to talk to.

We laughed a lot, and it felt like I had known him for much longer than just one evening.

A cozy couple | Source: Freepik

A cozy couple | Source: Freepik

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As we moved on to our main course, Jake looked at me with a smile. “So, Addison, how about we ask each other some more personal questions to break the ice further?”

“Sure, that sounds good,” I said. “What do you want to know?”

Food | Source: Unsplash

Food | Source: Unsplash

Jake leaned in slightly. “How about your one-to-five-year plan? What are your goals?”

I took a moment to think. “Well, I hope to advance in my career as a neurologist,” I began.

A woman staring at her man | Source: Freepik

A woman staring at her man | Source: Freepik

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“Maybe get promoted to a senior position. I also want to decorate my apartment; it feels too plain right now,” I continued. “I’ve been thinking about getting a pet, maybe a cat or a small dog. And I’d love to travel more, see new places, and experience different cultures. Oh, and I want to expand my bookshelf with my favorite novels. I love reading!”

Pile of books and cup on top | Source: Unsplash

Pile of books and cup on top | Source: Unsplash

“That sounds wonderful. You have a lot of exciting plans!” he grinned.

“What about you?” I asked, curious to hear about his future plans.

“I want to grow my freelance business,” Jake said. “Maybe open my own studio one day. I also love traveling, so I’d like to visit more countries. And, believe it or not, I’ve been thinking about getting a pet too. A dog, probably.”

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A dog | Source: Unsplash

A dog | Source: Unsplash

We laughed at the coincidence, and it felt nice to find common ground!

“So, how do you feel about marriage and family?” Jake further asked as he sipped his wine.

And this is where it all went horribly wrong.

A family | Source: Unsplash

A family | Source: Unsplash

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“Honestly, I’d love to find a partner to share my life with,” I told him, “someone who understands and supports me. But marriage isn’t a necessity for me. If it happens, great, but if not, that’s okay too. As for children, I don’t see myself having any. For now. I’m happy with my career and personal goals.”

Jake leaned forward, looking serious. “What if you found the perfect guy? How long before you’d marry him?”

Two people smiling at each other and standing close | Source: Freepik

Two people smiling at each other and standing close | Source: Freepik

“Three years,” I said. “I believe in building a strong foundation. Six months to really get to know someone, a year of serious dating, and a year and a half of living together before considering engagement or marriage.”

Jake’s face changed, his friendly expression replaced by a frown. He leaned back in his chair, crossing his arms. “Three years? That’s a long time. What if someone wants a quicker timeline?”

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An upset man | Source: Midjourney

An upset man | Source: Midjourney

I felt a knot forming in my stomach. “Well, uh, I think it’s important to take time to build a strong relationship. I’m pretty confident about my three-year-plan.”

Jake’s frown deepened, and he abruptly called the waitress. “Check, please,” he said curtly. She looked confused but quickly brought the bill.

A waitress | Source: Pexels

A waitress | Source: Pexels

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“Jake, what’s wrong?” I asked as he stood up, but he didn’t bother to answer. He paid and walked out of the restaurant without a glance back.

I sat there, stunned and hurt. What just happened?

Later, at home, I couldn’t stop thinking about the evening.

A woman staring at her reflection | Source: Pexels

A woman staring at her reflection | Source: Pexels

How could Jake just leave like that?

Deciding I needed answers, I messaged him.

I sent a selfie we took together and wrote, “Hey Jake, why did you leave so suddenly? I thought we were having a great time.”

A woman using her phone | Source: Unsplash

A woman using her phone | Source: Unsplash

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A few minutes later, his reply came: “Don’t contact me again. You’re indecisive and not serious about what you want.”

Then, he blocked me.

I stared at my phone in disbelief. Was I really that off base?

The next day at work, I noticed Nathan giving me strange glances. Gathering my courage, I decided to confront him.

A man holding a phone in his hands | Source: Unsplash

A man holding a phone in his hands | Source: Unsplash

“Nathan, what did Jake tell you? You know why he left, don’t you?” I asked, trying to keep my voice steady.

Nathan looked uncomfortable and shifted on his feet. “You messed it up, Addy,” he said. “Jake… told me you were wasting his time. He wanted something serious. He was looking for marriage, and you… you weren’t the best person for him. Sorry, I gotta go.”

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A sad doc | Source: Midjourney

A sad doc | Source: Midjourney

I couldn’t believe it.

During my lunch break, I called my best friend, Sophie.

“Hey, Addison. How did the date go?” was the first thing she asked.

A cheerful woman on video call | Source: Pexels

A cheerful woman on video call | Source: Pexels

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I sighed, feeling the weight of the evening pressing on me. “It started great, but then it ended terribly. Jake left abruptly after I talked about my three-year plan, and then he blocked me when I asked him why.”

Sophie’s eyes widened. “He did what? That’s ridiculous! What exactly happened?”

A sad young doctor | Source: Midjourney

A sad young doctor | Source: Midjourney

I recounted every detail, my voice trembling slightly as I relived the evening. When I finished, Sophie shook her head. “Addison, being honest about your expectations is important. If he couldn’t handle that, it’s his loss.”

“I can’t stop wondering if my three-year rule is really that strange, Sophie,” I admitted, my voice breaking a bit.

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An anxious doctor | Source: Midjourney

An anxious doctor | Source: Midjourney

“Not at all,” Sophie said firmly. “Everyone has their own timeline and needs. What matters is that you stay true to yourself. If he couldn’t appreciate that, he wasn’t the right guy for you.”

Her words wrapped around me like a comforting blanket. But it didn’t ease all my worries. Was I wrong to be upfront about my expectations? Should I have kept it to myself? All I know is that being honest about what I want is important, even if it means losing a date like Jake.

A doctor focused on her work | Source: Midjourney

A doctor focused on her work | Source: Midjourney

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What would you have done?

If you enjoyed this story, here’s another one: Julia is excited to surprise her husband on his birthday, but everything changes when she hears an unexpected voice. Hiding in the living room, her heart pounds as her husband’s laughter mingles with another woman’s. What will Julia uncover?

A couple | Source: Unsplash

A couple | Source: Unsplash

This work is inspired by real events and people, but it has been fictionalized for creative purposes. Names, characters, and details have been changed to protect privacy and enhance the narrative. Any resemblance to actual persons, living or dead, or actual events is purely coincidental and not intended by the author.

The author and publisher make no claims to the accuracy of events or the portrayal of characters and are not liable for any misinterpretation. This story is provided “as is,” and any opinions expressed are those of the characters and do not reflect the views of the author or publisher.

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