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.
Wealthy Woman Dresses up in Beggarly Clothes to Check Out Her Daughter’s Fiancé – Story of the Day
Monica told her mother, Vivienne, that she was engaged to a new man named Zach. The older woman couldn’t believe it, mainly because he was not wealthy, so she decided to dress up as a poor woman and investigate. She couldn’t have been more shocked at the scene she found in Zach’s house.
Vivienne’s daughter, Monica, had just stormed out of her house. They had a massive argument over Monica’s announcement. She was going to marry a man named Zach. Vivienne couldn’t believe it because she had no idea her daughter had broken up with her boyfriend, Anthony.
Anthony’s family wasn’t as wealthy as Monica’s family, but they were respected in the high society of Hartford. Vivienne dreamed of his daughter marrying well and never worrying about money. However, it seemed that Monica’s new man did not come from money at all. He lived in the small town of Mystic. Moreover, he was a fisherman, and his parents worked blue-collar jobs their entire lives.
For Illustration Purposes only. | Source: Pexels
That won’t do. She can’t marry him! Vivienne thought, trying to calm her rapidly-beating heart after the fight with Monica.
“I can’t marry Anthony, Mother! He cheated on me with at least three women in just two months! Do you want me to be miserable?!” Monica had asked in tears.
“That can’t be true!” Vivienne yelled back, and that’s when Monica decided to storm out of the house.
Vivienne sat in her living room and thought about what to do. She had to fix this somehow. If Anthony was really a cheater, it made sense that Monica became attracted to someone outside their society. But what if this Zach was with her for her family’s money? Men could be gold-diggers too.
She had to check out Zach without her daughter. It had to be a scenario where he was forced to act as himself and not the version he wanted Monica to see, so she came up with a plan.
The following day, Vivienne took a taxi and arrived in Mystic, Connecticut, wearing the most horrible clothes she could find in her old boxes. She wore a stained skirt which she purposely ripped on one side and a sweater that smelled like mothballs. It was perfect. She would see Zach and observe how he acted around regular people.
Luckily, Mystic was such a small town that everyone apparently knew where Zach lived. Vivienne just asked a lady at the local grocery store, and she pointed her in the general direction.
For Illustration Purposes only. | Source: Unsplash
She reached his house, which was worse than Vivienne could’ve imagined. It looked run down and had an unkempt garden. She saw beer bottles and cigarette buds lying around as she approached the front door. Monica has never seen this house before, Vivienne thought, convinced of it. There’s no way her daughter would’ve fallen for a man who lived like this.
She wanted to run but had to get this done, so she raised her finger and rang the doorbell. A man with a gray, sweat-stained shirt answered the door. He was clearly in his 20s. This had to be Zach. He had a bottle of beer in his hand and an unshaven face.
“Yeah?” the man said.
“Oh, hello,” Vivienne began tentatively. Now that she was there, she had no idea how to talk to him or what to say to discover what kind of personality he had.
“Lady, what do you want?” the man continued irately now.
“I’m sorry. I was wondering if you could help me. I’m a bit lost,” she finally blurted. “Are you Zach?”
“Yeah, that’s me. What do you want?” Zach asked and belched. Vivienne couldn’t help looking disgusted, and he laughed.
Suddenly, a woman started yelling from inside the house. “Zach! Where did you put my lighter? You’re always losing stuff! YOU IDIOT!”
Zach turned from Vivienne and started shouting at the woman. “I’m the idiot? I’M THE IDIOT! You’re the one that loses everything as soon as it gets here. I don’t know where you put it! Don’t blame it on me!”
For Illustration Purposes only. | Source: Pexels
“I can’t believe I’m still with someone like you! I’m going to leave you tonight!” the woman screamed some more, and Vivienne heard the distinct sound of breaking glass. She raised a hand to her chest.
“THE DAY YOU LEAVE WILL BE THE BEST OF MY LIFE, CRAZY WOMAN!” Zach snapped loudly and turned back to look at Vivienne. “Look, lady. Get to the point. I’m busy.”
“That’s your girlfriend?” Vivienne breathed. It was the only thing that came to her mind after that horrible display. These people were awful.
“None of your business, old woman. Now, go away,” he bellowed and slammed the door in her face. Vivienne jumped as the door closed and couldn’t believe her daughter was actually dating that man.
This is awful. Monica was not only going to get her heart broken again, but this man was clearly abusive and dangerous to women in general. Vivienne had to stop it. But first, she had to go back to Hartford, which meant finding a taxi in this small town.
She started walking the streets and noticed the other houses around the block. They were old and tiny, just like Zach’s, but others maintained them. At least, not everyone was bad in this area. They were covered in snow this time of the year. Suddenly, a woman came out of one of the houses, saw Vivienne, and waved.
Vivienne smiled and waved back, not knowing what else to do. The woman started walking towards her. She was around her age and had the kindest smile in the world.
“Hey, there! Do you need help? Are you lost?” the woman asked.
For Illustration Purposes only. | Source: Pexels
“Oh, no. Don’t worry about it. I just need to find a taxi and go home,” Vivienne answered and tried to walk away. But the woman wouldn’t let her.
“Wait. I’m Georgia. It’s getting really cold out here, and sometimes, it’s hard to find a taxi on the main road. Come inside, and I’ll call one for you,” she suggested.
“I’m Vivienne. Nice to meet you. That’s such a kind offer, but I don’t know….”
“I insist,” the woman continued and urged Vivienne inside.
They chatted a while, and Georgia called the cab company in town. Apparently, all the drivers were busy, and none of them wanted to drive all the way to Hartford.
“Oh, dear. What should I do? I have to get to Hartford tonight,” Vivienne muttered, biting her bottom lip.
“A taxi from here to Hartford is so expensive. Are you sure? Maybe, you can stay here, and tomorrow, you can take the bus,” Georgia noted.
“Oh, it’s alright. Someone else is paying the taxi,” Vivienne lied. “It’s important for me to get home tonight.”
Just then, someone opened the front door and came in. “Hey, Ma!”
It was a handsome man in his 20s who looked remarkably like Georgia with a kind face and smile. Georgia hugged him and introduced him to Vivienne. He was visiting his mother and brought over fresh fish he had caught that day.
“Oh, boy. I meant to ask. Do you know anyone going to Hartford tonight?” Georgia asked her son after stashing the fish in the freezer.
For Illustration Purposes only. | Source: Pexels
The man stood in the middle of the living room and pursed his lips. “Oh, I don’t. Why?”
“Vivienne has to get there tonight, but none of the taxis in town want to take her,” Georgia replied.
“Well, why don’t I take her? I was thinking of going to Hartford this weekend and buying some stuff. But I guess tonight works too,” Georgia’s son offered.
“Oh, I wouldn’t want to put you out. You look tired,” Vivienne muttered, embarrassed.
“Don’t worry about it. Let’s go,” the man insisted and guided Vivienne to his car. It was an old pickup, but he assured her it worked perfectly and would get them to their destination.
They talked during the more-than-one-hour drive to Hartford, and Vivienne was pleasantly surprised by his kind demeanor. Not many people would have offered an older woman a ride just like that, and she hadn’t talked about paying him. He was a kind, hard-working man.
Well, not everyone in that town is as awful as Monica’s new boyfriend. Why couldn’t she meet a boy like this? Vivienne was lost in thought as they entered the city.
“Ma’am. Where exactly are you going? I can take you anywhere,” the man wondered.
“Oh, there’s this gated community…,” Vivienne began, giving him the directions to her area. But she told him to stop at the gates instead of leading him to her house.
For Illustration Purposes only. | Source: Pexels
“Here! Have some money for the ride. It’s what I would’ve paid the taxi,” she said, holding out some cash in her hand and opening the door with her other hand.
“No, no. I couldn’t. I was already coming here anyway,” the man rejected her offer.
Vivienne tried to insist. “Please, take it.”
“No, ma’am. I really couldn’t. I used this ride as an excuse to see my girlfriend, who lives around the area. I should thank you!” the man laughed, and Vivienne joined him.
“Well, then. I appreciate your kindness,” she finally said before getting out of the truck and waving goodbye at the young man.
Oh, I never even asked his name. Jesus, I forgot all my manners, she thought after reaching her house.
Her meeting with Monica’s horrible boyfriend had truly shaken her, but at least, she met some great people that got her home safely. Obviously, she knew that money wasn’t everything, and many average folks were great people. But her daughter had made a colossal mistake.
Why couldn’t she have picked someone like Georgia’s son? He was pretty nice, Vivienne thought as she changed out of the old clothes and into her pajamas.
For Illustration Purposes only. | Source: Pexels
Suddenly, her phone pinged with a message. It was Monica. She said that she was bringing her boyfriend for dinner tomorrow night and hoped Vivienne would be nice.
“Oh, dear. I’m going to have to break your heart tomorrow. But you definitely can’t marry that man,” she muttered out loud, looking intently at her phone.
The following night, Vivienne was worried. Her daughter’s car had just pulled into her driveway, and Zach was coming with her. She had no idea how to explain what she did yesterday and how she ended up at that man’s house. But Monica would have to see reason. That horrible man was sweaty, rude, and had a girlfriend.
There was a knock on the front door, and Vivienne breathed deeply to gather her courage. She was about to start a huge fight with that man, and Monica had to listen to her. But when the older woman opened the door, her mouth dropped. No arguments or screams came out — just a tiny squeak.
“Mom?” Monica asked, frowning at her mother.
The man standing beside her was not that sweaty Zach she had met the previous day. It was Georgia’s son!
For Illustration Purposes only. | Source: Pexels
“Ma’am?” the man asked and looked at Monica with a confused expression. “This is your mother? I gave her a ride from Mystic last night.”
“What? Mom, what were you doing at Mystic?” Monica wondered, placing her hand on her waist.
“Oh, dear. Come in! Come in! This is your boyfriend, Zach?” Vivienne inquired as she guided them inside quickly, breathing heavily. She was ecstatic.
“Yes, Mom. This is Zach. But did you meet him yesterday?” her daughter asked again, refusing to let her change the subject. They both removed their coats, and Vivienne was smiling at them with the most relieved smile in the world.
“Yes, dear. It’s a long story. Sit down…,” she told them and explained everything that happened the day before, including how Zach ended up driving her back to Hartford.
There were two people named Zach in the town of Mystic, and the lady at the store only knew one of them. The rude one. Monica found the whole story hilarious and their original fight had already been forgotten by the time Vivienne finished.
For Illustration Purposes only. | Source: Pexels
The whole night, Vivienne was so friendly to Monica’s Zach. They had dinner and enjoyed a wonderful time. Before the couple left, Vivienne told Monica that she approved and would pay for their wedding if they desired. The older woman never judged Zach for being a fisherman because he treated her daughter like a princess.
Besides, after meeting that sweaty Zach, anyone else was infinitely better.
What can we learn from this story?
- Don’t judge others based on their financial status. Money doesn’t mean anything in the end. Some horrible people have tons of money, and some of the greatest might be working paycheck to paycheck.
- Don’t assume you know what’s best for your children. Some parents think they know what would make their kids happy, but that’s not always the case.
Share this story with your friends. It might brighten their day and inspire them.
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