Eight-year-old David was begging for money outside a mall when he noticed a homeless man staring at him for a long time. He ran away thinking this person was dangerous, but he caught him and explained something shocking about the boy’s past.
David Donaldson stood outside International Plaza and Bay Street in Tampa, Florida, and couldn’t hold back his tears. His face was covered in wet streaks, and most people only looked at him for a second before they continued walking. He was there to try to raise money for his mother’s funeral.
David’s mother died after a long battle with cancer, and the funeral home was waiting for the money to pay for everything. The manager was worried about the kid, but David had lied to him, explaining that his uncle was coming soon and would be paying for everything.
For illustration purposes only | Source: Pexels
Sadly, David didn’t have any family left. He was staying at the apartment, but the rent was due soon. He would not be able to pay, and others would soon discover what was going on. They would call CPS, and he would go into the system.
He hated that idea. That’s why he was at the mall, begging people for money. Some shoppers were familiar with the little boy because he also tried to raise funds throughout his mother’s treatment. They would give him a dollar or two before calling the cops. Luckily, David was able to get away from them.
But now, his mother was finally gone, and she deserved to have a nice service. So, once again, he stood outside there with a sign where he wrote what he needed.
After a long sniffle, David dried his tears, thinking that people might be avoiding him because of his crying. He needed that money, so he had to be brave and stop. But once he cleared his eyes using his hands, David saw someone strange. A man was looking at him from the other side of the street. His stare was unnerving.
The man was dressed in tattered clothing, and it was clear he was homeless. David feared he would become like him soon. But an even scarier thought crossed his mind. What if he wants to steal my money? No! My mom needs it!
David gathered his hat from the floor where people had thrown some extra change and started counting. He placed them inside his pocket quickly and raised his head just to see the man cross the street and walk directly toward him.
The boy’s blood went cold, but he had to think fast. That’s when he stood and raced out of there. He could hear the heavy footsteps of the man running after him, and the man yelled, “Wait boy, I want to talk to you!”
“No! This is my mother’s money! Go away!” David screamed back but didn’t slow his pace.
For illustration purposes only | Source: Pexels
“I don’t want your money, boy! Please, stop!”
The boy didn’t listen, but unfortunately, he entered a dead-end alley and couldn’t escape. “Please, sir. This money is very important. My mother just died, and I need to pay for the funeral,” David pleaded with the man, clutching his right hand over his right pocket where he kept the cash.
The man stopped and approached him slowly now. David could see his unclean state and ragged shirt, but there was something familiar about his face. He also had kind eyes. Maybe he wasn’t lying.
“Again, I don’t want your money, boy. I read your sign. You said your mother died? Can you tell me her name?” the man asked, smiling slightly.
“Maria,” David answered shyly.
“What about you? What’s your name?”
“David Donaldson.”
The man closed his eyes and nodded. Then he looked at the ground, and David could hear his heavy breathing.“Oh, man,” the man whispered and started crying.
“Sir, are you ok? Did you know my mother?” David asked, taking a small step towards the man.
“Yes. I knew her,” the man replied. “But I can’t believe she’s gone. I’m a horrible man.”
“What?”
For illustration purposes only | Source: Pexels
“Maria… I mean, your mother was my girlfriend around nine years ago. My name is Charlie Donaldson,” the man answered and looked up at him. David could see the tears in his eyes and the sadness in his expression.
“Why do you have my last name?” David questioned, although the eight-year-old was no fool. He already guessed the reason.
“I’m pretty sure I’m your father, kid,” the man revealed.
The boy had no idea what to say, but it was probably true. The man’s face had looked familiar because they shared the same green eyes.
“Ok, so you don’t want to take my money,” David added, just to confirm.
Charlie laughed bitterly. “No, David. I would never do that. I fell on hard times, and that’s why I’m homeless, but I would not take money from a child. Besides, you need to pay for Maria’s funeral, right? That’s what your sign said.”
“Yeah. It’s expensive,” the boy said, scratching the back of his head with one hand.
“Let me ask you something else. Who are you staying with? An aunt or an uncle?”
“No one.”
“Maria told me she had a sister,” Charlie stated with a frown. He wiped the tears that had streaked his face and looked straight at the boy.
For illustration purposes only | Source: Pexels
“No. I never met anyone, or maybe, they don’t know Mom died,” David continued, not knowing what else to say. It was the truth. It had always been just the two of them.
“And why are you on the streets? Shouldn’t CPS have taken you in?”
“I lied to some people. I told them my uncle was coming soon. I guess they didn’t call anyone,” David answered. But suddenly, he was curious about something. “If you’re my father, why weren’t you in my life?”
“That’s a long story,” Charlie began and said that he had run away as soon as Maria told him she was pregnant. He didn’t want the responsibility. “But in the end, it was the worst thing I ever did. Karma got to me, and I got mixed up with some bad people. I should’ve stayed with your mother and been a father to you.”
They talked more in that dead-end alley and even had a few laughs despite their sad circumstances. Finally, David had an idea. “Why don’t you come live with me so that I won’t be taken away? But on the condition that you will get a job and help me out. I’m a kid. I can’t do anything without an adult without raising suspicion.”
For illustration purposes only | Source: Pexels
“Are you sure? Do you have a house?”
“An apartment. But rent is due at the end of the month. I don’t have the money. I still have to pay for Mom’s funeral,” David continued.
Charlie thought about it for several minutes. He didn’t have a home and had no idea how to raise a kid. But it was a deal he couldn’t pass up. So he moved in with David, and now that he had an address, he could apply for jobs.
Together, they raised enough for a simple funeral for Maria, and they bonded when Charlie told him stories of their time together. David reciprocated and recounted all the things they did together. Eventually, Charlie found a job at Target and paid rent a few weeks later, as the landlord gave them an extension.
David was able to go back to school instead of begging for alms every day. In the end, they thought of each other as family even if they met under the oddest of circumstances.
What can we learn from this story?
- Don’t run from your responsibilities. Not everyone is ready to have kids, but you can’t run away from your duties.
- It’s never too late to do the right thing. Charlie moved in with David and paid for everything he could, so the kid would not have to be alone.
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Homeless Man Asked Me to Buy Him Coffee on His Birthday — Hours Later, He Sat Next to Me in First Class
Jimmy was stunned when the homeless man he’d bought coffee for earlier boarded the plane and sat beside him in first class. Who was he and why was he asking for money in the first place?
I’d never thought much about destiny until I met Kathy.
Three months ago, she walked into my life, and within weeks, she became my world. People called me crazy for proposing after just a month, but I couldn’t ignore the way everything fell into place with her.
A woman sitting in her living room | Source: Midjourney
We shared the same outlook on life, the same love for skiing, and even a mutual obsession with science fiction novels. It felt like the universe was nudging me, whispering, she’s the one.
Now, here I was, flying out to meet her parents for the first time.
Kathy warned me about her dad, David. She called him a stern man who didn’t give his approval easily. But she also insisted he had a good heart and loved her more than anything.
A woman sitting with her phone in her hand | Source: Midjourney
To be honest, I was scared. I knew I just had one shot to prove I was worthy of his daughter, and I didn’t want to mess it up.
I’d arrived at the airport too early, nerves pushing me to leave home long before I needed to. To kill time, I ducked into a cozy little coffee shop across the street.
The hum of conversations and the aroma of freshly brewed coffee were a welcome distraction from the thoughts swirling in my head.
That’s when I noticed him.
A man sitting in a coffee shop | Source: Midjourney
The man shuffled in, wearing tattered clothes. His face had wrinkles that showed he had worked hard all his life. His shoulders were slightly hunched, and his eyes, though tired, darted around the room like he was searching for something.
I watched as he approached a few tables, speaking softly to the people seated there.
People in a coffee shop | Source: Midjourney
Most people shook their heads, avoided eye contact, or offered an awkward apology. Then, he stopped in front of my table.
“Excuse me,” he said politely. “Could you spare some change? Just enough for a coffee.”
I hesitated. My first instinct was to decline. Not because I didn’t care, but because I wasn’t sure how much to trust him. You know, some people are genuine while others are just looking for handouts.
But something about him felt different. He wasn’t pushy, and he looked embarrassed to be asking.
A close-up shot of an older man | Source: Midjourney
“What kind of coffee do you want?” I asked.
“Jamaican Blue Mountain,” he said, almost sheepishly. “I’ve heard it’s really good.”
I almost laughed. It was the priciest option on the menu. For a moment, I thought he might be joking. But the way he looked at me made me stop.
“Why that one?” I asked.
“It’s my birthday,” he smiled. “Always wanted to try it. Figured… why not today?”
A part of me wanted to roll my eyes.
Sure, it’s your birthday, I thought.
But another part of me decided to believe him.
A man lost in deep thought | Source: Midjourney
“Alright,” I said, standing up. “Let’s get you that coffee.”
His face lit up with a genuine smile. “Thank you,” he said.
I didn’t just buy him the coffee, though. I added a slice of cake to the order because, honestly, what’s a birthday without cake? When I handed him the tray, I gestured to the empty chair at my table.
“Sit,” I said. “Tell me your story.”
For a second, he hesitated, like he wasn’t sure if I meant it.
A coffee mug on a table | Source: Pexels
But then he sat down, cradling the coffee cup like it was something sacred. And he started to talk.
His name was David, and he’d lost everything years ago, including his family, his job, and even his home. Betrayal and bad luck had played their parts, but he didn’t make excuses.
He spoke plainly, with a kind of raw honesty that made it impossible not to listen.
As I sat there, I realized this wasn’t just a man looking for a handout. This was someone who’d been broken by life but hadn’t given up.
A close-up shot of an older man’s eye | Source: Pexels
By the time he finished his story, I felt a lump in my throat I couldn’t quite swallow. I slipped him $100 before leaving, but he tried to refuse it.
“Consider this a gift from my side, man,” I told him. “And happy birthday!”
I walked out of that café thinking I’d done a small, good thing for a stranger. I’d never imagined I’d see him again. Or that he’d turn my entire world upside down just a few hours later.
A man looking straight ahead | Source: Midjourney
The airport was buzzing with its usual chaos as I sat in the first-class waiting area, sipping another cup of coffee.
My nerves about meeting Kathy’s parents had calmed somewhat, but the thought of her father loomed large in my mind. What if he didn’t like me? What if he thought I wasn’t good enough for her?
I picked up my phone to text Kathy, who had already reached her parents’ place.
I’m super nervous, I wrote. How’s it going there?
Everything’s great, she texted back. I’m sure Dad’s going to love you.
When the boarding call came, I joined the line and found my seat near the window.
The view from an airplane’s window | Source: Pexels
First class felt like a luxury I didn’t deserve, but Kathy insisted I spoil myself for once. As I buckled in and glanced around, I couldn’t help but think about the man from the café. His story had stuck with me.
I hoped the $100 I’d given him would make his birthday a little brighter.
Just as I was settling in, a figure stepped into the aisle. My heart nearly stopped as I looked at his face.
A man sitting in an airplane | Source: Midjourney
It was him. The same man from the café.
But he wasn’t wearing the tattered clothes from earlier.
No, this man was in a sharp, tailored suit, his hair neatly combed, and a gleaming watch on his wrist.
He caught my eye and smirked.
“Mind if I join you?” he asked casually, sliding into the seat next to me.
I stared, my brain refusing to process the scene in front of me. “What… what’s going on here?”
He leaned back, a sly grin on his face. “Let’s call it… a test.”
An older man in an airplane | Source: Midjourney
“A test?” I repeated. “What are you talking about?”
The man chuckled softly as he pulled out a sleek notebook from his bag.
“Let me introduce myself properly. I’m David.” He paused, watching my reaction. “Kathy’s father.”
“Wait… you’re her dad?” I blurted out. “The one I’m flying out to meet?”
“The very same,” he said, still grinning. “You see, I’ve always believed in a hands-on approach. I wanted to see who my daughter’s fiancé really is outside the polished dinner introductions and carefully rehearsed answers.”
A close-up shot of an older man’s face | Source: Midjourney
I couldn’t believe it. Why didn’t Kathy tell me about this? Was she a part of this plan?
“So, this was all an act?” I asked.
“A necessary one,” he replied calmly. “It’s easy to show kindness when everyone’s watching. But I wanted to know how you’d treat a stranger, especially one who seemed to have nothing to offer you. Turns out, you passed the first part.”
“The first part?” I echoed. “How many parts are there?”
He opened the notebook and handed me a pen. “Just one more. Write a letter to Kathy.”
“A letter?”
A young man looking straight ahead | Source: Midjourney
“Yes,” he said, leaning back in his seat. “Tell her why you love her, why you want to marry her, and how you’ll take care of her. Don’t overthink it. Be honest.”
I stared at the blank page as beads of sweat formed on my temples. This wasn’t what I’d signed up for. But as much as I wanted to protest, I knew I couldn’t.
So, I started writing.
At first, the words came slowly, stumbling over thoughts and emotions. But soon, the pen seemed to move on its own.
A man writing a letter | Source: Pexels
I wrote about how Kathy made me feel complete, how her laughter could brighten my darkest days, and how I wanted to build a life with her filled with trust and joy.
By the time I finished, my hand ached, but my heart felt lighter.
However, I still wasn’t sure if I’d pass the test. What if this was a trick question? What if David’s test wasn’t as simple as it looked?
A close-up shot of a man sitting near in the window seat | Source: Midjourney
After I handed him the notebook, he looked at it for a moment. Then, he looked up with a smile.
“You passed,” he said. “Welcome to the family.”
I felt so relieved after hearing those words.
This man, who had just tested me in the most unexpected way, extended his hand. I shook it firmly, knowing I had crossed the final hurdle.
“Now, let’s see how well you do at home,” he said.
An older man in a black suit | Source: Midjourney
When we finally landed and deboarded, I was both physically and mentally exhausted. As we walked through the terminal, I tried to steady my breathing, hoping I’d done enough to impress him, but my nerves were still fraying at the edges.
The drive to Kathy’s parents’ house was quiet. She and her mother were waiting for us there.
Meanwhile, my mind was racing with thoughts of what the evening would bring. I wasn’t just meeting her parents anymore. I had passed the “test.” But what did that even mean? Would David’s approval be enough? What would happen at their home?
Cars on a road | Source: Pexels
When we arrived, Kathy’s mother, Susan, greeted us warmly. Kathy’s brothers and sister were there too.
David, however, kept his usual serious demeanor, eyeing me across the table. I couldn’t tell if he was still evaluating me or simply reserving judgment.
Dinner was an uncomfortable affair, with everyone making polite conversation while David sat back, watching everything closely.
Every time I spoke, he would nod or grunt, never offering much in return. Kathy’s siblings were easygoing, but David’s silence was almost deafening.
I couldn’t help but wonder, Did I really pass?
A man sitting for dinner in his house | Source: Midjourney
As the meal drew to a close, David set down his wine glass and cleared his throat.
“You’ve done well, Jimmy,” he said. “You’ve shown me who you really are. And that means something.”
Kathy squeezed my hand under the table.
“I’ve always known you were the right one for me,” she whispered.
“I’ve seen enough to know he’ll take care of you,” he said while smiling at his daughter. “You’ve got my blessing.”
A man smiling at his daughter | Source: Midjourney
I was super happy at that point, but there was something unspoken in the way David looked at me.
After dinner, as Kathy and I helped her parents clean up, I thought everything had fallen into place.
That’s when I stumbled upon a folded piece of paper on the counter.
As I unfolded it, I realized it was a receipt for a cup of coffee from the café I had visited earlier that morning. The one where I met David.
A young man looking at a receipt | Source: Midjourney
The receipt wasn’t for the coffee I bought for David, though. There was an additional charge at the bottom.
“Extra donation — $100.”
I picked it up and turned to Kathy.
“What’s this?” I asked her.
“Oh, that’s my dad’s way of tying up loose ends.”
I frowned, confused. “Loose ends?”
She leaned against the counter, her eyes twinkling. “You gave him $100 at the café, remember? He didn’t keep it. He handed it to the café staff and told them to count it as an extra donation after you left.”
“And… how do you know that? Did you know about his plan all along? Were you a part of it?”
A man talking to his fiancée | Source: Midjourney
She gave me a sly smile.
“Well, I was,” she said. “You didn’t think it was just about the coffee, did you? And how do you think Dad knew about your flight? Of course, it was me, Jimmy.”
At that point, I realized I wasn’t marrying into a regular family. These people were very special, and they wanted me to realize the importance of generosity. And what it meant to be a part of this family
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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