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.
Rich Man Falls in Love with Homeless Girl He Sees on the Street and Rushes to Find Her — Story of the Day
He saw a girl begging on the sidewalk and somehow couldn’t get her face out of his mind. He had to know her story.
Wealthy businessman Roger Landers was often annoyed by the sight of the homeless begging on the street outside his office building. There seemed to be more and more of them each year, he reflected.
As he passed a young woman huddled against a wall, a kindly soul dropped a coin in her cup. The woman looked up and smiled at her benefactor and that smile pierced Roger to the heart. In one second, that huddled anonymous annoyance became a lovely radiant woman.
For illustration purposes only. | Source: Unsplash
Roger walked into the building and that moment when the girl’s face was transformed by her smile replayed over and over in his mind. He found himself wondering who she was, what had driven her to live in the pitiless streets of L.A.?
For the rest of the week, Roger found himself almost obsessed by the young homeless woman. He watched her surreptitiously, and once when he dropped a coin in her cup, watched that miraculous transformation at close quarters.
Love can sometimes lurk in the most unexpected places.
He found himself thinking about her, inventing stories about her, little fantasies in which he discovered she was really a reporter writing about homelessness at close hand, or a deeply committed actress preparing for a role…
Finally, on Friday afternoon, after he wrapped his work for the day and dismissed his employees, Roger did what he’d been longing to do all week. He walked up to the girl sitting on the sidewalk and talked to her.
For illustration purposes only. | Source: Unsplash
“Hi,” he said awkwardly. “Would it be okay if I bought you a cup of coffee? You look really cold.” The girl lifted up her face and smiled at him.
“Thank you,” she said sweetly. “I’d like that.” Roger was struck by her low educated voice and her grace as she got to her feet. She was tiny, he realized, a petite 5′ 3″ next to his towering 6′ 2″.
He walked her to a nearby coffee shop and ordered her hot food to go with her coffee. Once again Roger was surprised by her delicate gestures, her manners. This was an educated girl. How had she ended up on the streets?
When Roger saw color flood back into the girl’s face after she finished her hot soup, her grilled sandwich, and her coffee, he asked her exactly that. “How did this happen to you? Living on the streets?”
The girl looked him straight in the eye. A wry smile twisted her lips. “I was stupid, and trusting,” she said. “It’s not an original story. I was in love with this boy in my hometown — Idaho — if you can believe it.
For illustration purposes only. | Source: Unsplash
“My parents disapproved of him, which only made him even more romantic and attractive to me… To cut a long story short, he convinced me to withdraw my college funds and run away with him to L.A. He was going to be a movie star, and I’d be a screenwriter…”
Roger shook his head sadly. “A lot of people come out here every year, less than a handful make it!” he commented.
“Well, I’ll never know.” A tinge of bitterness colored the girl’s voice. “The first night in L.A., we booked into a motel. When I woke up in the morning Kevin was gone, so was my money and everything I had.”
Roger gasped. “Did you go to the police? Call your family?” The girl was shaking her head, tears in her eyes.
“I was too ashamed. I made a deal with the motel manager. She let me sleep in the storeroom and I cleaned the rooms. Some of the guests gave me tips, and I managed to eat. But then her husband started trying…” The girl shook her head. “You know how it is. I left the motel and ended up here, on the streets.”
For illustration purposes only. | Source: Pixabay
“What’s your name?” Roger asked gently.
“Emma,” the girl said with one of those radiant smiles. “Emma Sinclair from Preston, Idaho!”
“Well, Emma Sinclair from Preston, Idaho,” Roger smiled back. “I’m Roger Landers from Los Angeles, California, and I’m sending you home.”
Roger took Emma into a nearby mall and he bought her several outfits and a suitcase. He waited at the food court while she changed and came out of the restroom transformed.
He drove her to the bus station and bought her a bus ticket home. He tucked a $100 bill in her hand. “Listen,” he said. “Don’t let any more charming rascals talk you into coming to L.A., OK?”
For illustration purposes only. | Source: Unsplash
Emma was crying and smiling through her tears. She reached up and gave Roger a hug. “Thank you, thank you, and God bless you!”
Roger watched her board the bus with a sinking feeling in his heart. Why did he feel that this was a mistake? He wanted to run after that bus, beg Emma to stay… What was happening to him?
That night, Roger realized that the petite waif with the glowing smile had stolen his heart. “If I let her go, I’ll regret it for the rest of my life!” he told himself. “She’s special, and I love her.”
Two days later, Roger was driving into Preston, Idaho. He stopped at the police station and asked where he could find Emma Sinclair. “Emma?” asked one of the deputies suspiciously. “What do you want with Emma?”
For illustration purposes only. | Source: Unsplash
Roger blushed. “Well, you see, I met her in LA, and I wanted to see if she was alright…”
The deputy looked him up and down. “You can find Emma at her mom’s laundromat, two doors down. I’m coming with you. I don’t want any more trouble for Emma!”
Roger’s heart was beating fast as he walked into the laundromat and saw Emma. She looked up and her face lit up. At that moment, Roger knew she had been feeling the same way: they belonged together!
So just three weeks after she returned home, Emma headed back to LA once again, but this time she was with a man who loved and cherished her. By the end of the year, Roger and Emma were married, and she became involved in a program to help runaways find their way home.
For illustration purposes only. | Source: Unsplash
What can we learn from this story?
- Helping others can be a transformative experience. Roger helped Emma, and in the process, he found his own way to life-long happiness.
- Love can sometimes lurk in the most unexpected places. Roger found love with a homeless waif when everyone expected him to marry a socialite.
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