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.

My Parents Arranged a Marriage for Me, So I Decided to Test My Wealthy Fiancé

When Nadia returns home from college abroad, she has no choice but to agree to an arranged marriage to a wealthy man—a man chosen by her parents. But as the tentative date for their wedding draws closer, Nadia decides to test him, to truly understand who she’s marrying.

I never imagined that I’d find myself disguised as a homeless woman, sitting on a sidewalk outside of a restaurant. I sat there, hunched with a shawl wrapped around my shoulders.

A woman sitting on the floor | Source: Pexels

People passed me without paying any attention, as I watched for the sleek black car that often carried my fiancé, Danny.

Despite it being the 21st century, in my culture, arranged marriage still holds its own.

A black Mercedes-Benz | Source: Pexels

But I had been studying in America for the past four years, and my ideal of independence and personal freedom was something very different from what I had left home with.

Now, I found myself rebelling at every turn.

A woman in a red coat | Source: Pexels

When my parents first broke the news of my engagement to Danny, I was still ensconced in the States—my mind buzzing with new ideologies and lectures on autonomy.

“Now that you’ve been abroad and have studied,” my mother said, “it’s time for you to become a wife.”

I tried to protest, but it always fell on deaf ears.

A smiling woman in a white dress | Source: Pexels

“Nadia,” my mother said, “there is no choice here. Your father and I have done our research. Danny is a good one. He will take care of you.”

My mother moved around the kitchen, mixing a concoction of spices as she began to cook dinner.

Assorted cooking spices | Source: Pexels

“And that’s just it?” I asked, making some tea. “I have to marry this man?”

She nodded and smiled at me.

“Nadia, your father and I did it—we had an arranged marriage, and everything turned out well for us.”

A bride and groom holding hands | Source: Pexels

Now, I was faced with meeting a stranger whom I was going to marry—a stranger and his affluent family.

“You’re going to meet him soon, and his family. They own a line of restaurants, darling. They’re always going out of their way to help people.”

Restaurant interior | Source: Pexels

A few days later, we were all settled around the dining table. It was the first time that I was meeting Danny, and I had no idea what to expect.

When I stepped out of the house, he was there in the driveway, dressed in a suit—holding a gift bag and flowers.

A bouquet of roses | Source: Pexels

On first impression, he was good-looking, but I needed him to be more than just a nice face to look at.

This man was going to be my husband. I was stuck with him. And judging from the way my parents were behaving, I didn’t have a choice in the matter.

A man wearing a suit | Source: Pexels

As my father welcomed Danny and his parents into our home, my mother brought out a tray of tea and sweets.

“I didn’t know what you’d like,” she said, “so I got everything.”

Tea on a tray | Source: Unsplash

Danny smiled at her; he seemed to genuinely care about impressing my parents. We exchanged polite conversation during the tea, and when it was time for us to have dinner, we sat around the table.

“Danny,” my father said, pointing to the head of the table, “sit here.”

My mother began to fuss over Danny and his family, ensuring that she piled their plates high with food.

A table full of food | Source: Pexels

“I need you to leave here knowing that you’ve been fed,” she said.

I poured myself a glass of juice. It was going to be a long meal.

“Why did you decide to study in America?” Danny asked me, frowning over his glass of water. “Didn’t you want to stay around family?”

Juice in glass bottles | Source: Pexels

“I applied not thinking that I could get in,” I admitted. “But then I did, and I wanted it to be a new challenge for me.”

“But being away for so long?” he pressed. “I bet you spent time in the library.”

“It was just four years. I came home a few times anyway.”

A library | Source: Pexels

“Family is very important to me, Nadia,” he said firmly.

I looked at my mother, who refused to meet my eye. Without me replying to Danny, the silence took over for a few moments. Only the sound of scraping cutlery and chewing could be heard.

A woman eating | Source: Unsplash

“Tell Nadia about your charity,” my father said, beaming at me.

“Oh!” Danny’s mother exclaimed, quickly putting her fork down.

She went on at length about how Danny feeds homeless people all the time, and that he had scheduled a roster for different areas around us.

Bags of food | Source: Unsplash

“Nobody will go hungry if we can help it,” Danny’s mother said.

My goodness, I thought to myself as I dug into my chicken. Do I really need to bear this for the rest of my life?

The dinner ended, and my husband-to-be left the house.

A plate of food | Source: Unsplash

“Don’t you love him?” my mother asked as we washed up the dishes and cleaned the kitchen.

“I don’t know him, Mom,” I said.

“But you will,” she replied, drying the plates with a dish towel. “You will get to know him soon.”

A person washing a glass | Source: Pexels

I didn’t have the energy to deal with it further. I went to my bedroom and sat down, wondering how I could just give in to tradition after having been away and free for so long.

I yearned for my college dorm and the liberation that had come with it. But I also knew that I would have to let go of that.

A woman in her room | Source: Pexels

Instead, I had to wait for the day of my arranged marriage. As the months closed in, the wedding drew closer, and I began to get anxious—needing pills to sleep.

I didn’t know how I was going to marry Danny, knowing only the bare minimum about him.

One morning, while pouring myself some cereal, I decided that I would dress like a homeless person and wait outside the restaurant that Danny was based at. I needed to see how he would react to someone in need.

A bowl of cereal | Source: Pexels

As the car approached, I huddled into my disguise, my voice hoarse as Danny stepped out of the car.

“Excuse me, Sir,” I said. “Could you spare…”

Danny paused, his brows furrowing slightly.

“Ma’am, what do you need? I can’t just hand you money or food for the day. We need to help you long-term.”

A man frowning | Source: Pexels

My heart tightened.

“There’s a shelter not far from here,” he said. “I can take you there, my mother volunteers there, too. You’ll be safe there. You can get a meal, a shower, clean clothing, and we can talk about getting you on your feet.”

I stood up and pulled my shawl away, revealing myself to him.

“Nadia?” he exclaimed, his eyes wide. “What are you doing?”

A shocked man | Source: Pexels

“I was testing you, Danny,” I said. “I wanted to see if you really are the person they say you are. I just needed to know. How else can I marry you?”

Danny looked stunned, then a wry smile spread across his face.

“I guess I should be honest too, then. I’ve been horrible on purpose, hoping you’d call off the wedding.”

His candidness took me aback.

A smiling man | Source: Pexels

“Why would you do that?” I asked.

Danny sighed, running a hand through his hair as he silenced his ringing phone.

“Because I thought it was all a farce. I didn’t want to be part of an arrangement. Not really. I knew that it needed to be done, because of my age. But I’ve wanted love. I’ve wanted to marry for love.”

A man holding a phone | Source: Pexels

As we sat down on a nearby bench, Danny opened up about his past.

“The parents you met are my adopted parents. My mother died when I was very young, and they took me in. I’ve built my entire persona to help people who are where I once was. It’s not just philanthropy—it’s personal.”

His words echoed in the cold air—each syllable heavy with emotion.

“Yes, I am successful. But I never wanted to use that success as leverage for a marriage. I wanted someone to see me, not my money or my past.”

Flowers on a grave | Source: Pexels

We talked through the evening, unraveling the misunderstandings and the pressure from our families. It was the first time we truly connected, seeing each other beyond the expectations set upon us.

In the weeks that followed, we began dating—real dates, filled with genuine laughter and shared dreams. Our parents saw the change in us, the way we looked at each other with newfound respect and affection.

Soon, we’ll be married, but now, I’m content with the reality of it.

A couple holding hands | Source: Pexels

What would you have done?

If you enjoyed this story, here’s another one:

When Elle’s mother passes away, she moves through the funeral in a daze. But then, she stumbles upon a man who closely resembles her. When he approaches her, he reveals that he is her biological father—who had been hidden away all this time. Elle doesn’t know whether she should tell her father and risk losing the only other parent she has ever known.

Read the full story here.

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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