Sometimes people have to go to extremes to attract the right people, and this is the case in the following stories. The wealthy characters in these stories donned cheap clothes, begged, and even pretended to be homeless to see the true nature of their loved ones, and the results are astonishing!
In the following stories, our protagonists are confronted with wealthy and pretentious parents who believe their daughters deserve wealthy suitors or nothing less, wealthy men who pretend to be good people to attract the richest girls, and girlfriends who only want to marry wealthy men. Let’s get to the heart of the matter:
Three people dressed in dilapidated clothes | Source: Midjourney
1. My son wasn’t good enough for his fiancée’s parents until they found out the truth about him
When I, Sam Sutton, invented an unbreakable engine sealant, I never imagined it would one day impact my son Will’s love life. Money poured in, radically changing things for us, but I quickly learned that money couldn’t buy everything.
A man working on an experiment | Source: Unsplash
There are two things in life that money can’t buy: love and health. I learned the first the most painful way when my wife, Rain, died despite all the wealth in the world, and I learned the second when Will grew up.
I had to raise my only child and son as a single father, and I made some mistakes along the way, including spoiling him. But he grew up kind, loving, and upright. In high school, he became popular, even though it was obvious that people were attracted to him not for his character, looks, or kindness, but for my money.
A high school student | Source: Pexels
The girls were particularly interested in him, but Will quickly realized they weren’t interested in HIM; they wanted the travel, the luxury, the lifestyle. One night, he came to me with a broken heart.
“Dad, the girl I love is only interested in money.”
“Then let her go, my son,” I told him, hating to see him so hurt.
After that, Will kept his distance from superficial friendships.
Then one night, he surprised me with a plan. “Dad, when I go to Yale, I want people to think I’m poor, a scholarship student.”
“A scholarship student? Why?”
A shocked man reacts to someone off camera | Source: Midjourney
“If people think I’m poor, they’ll only like me if they really care about me,” he explained.
I admired his idea, and we went all in. We bought him some scruffy, secondhand clothes, and he went to Yale looking like he didn’t have a penny in his pocket! The plan worked perfectly! Will made some real friends and met a girl he really liked, Edwina, or Eddy, as we called her.
By the time he was third grade, my son was in love and ready to propose! I was worried he was too young, but he was confident. Eddy said yes, and everything seemed perfect… until he met the girl’s parents, Marta and Farlow.
A happy elderly couple | Source: Freepik
They were rich, proud, and completely unimpressed with Will. When he visited them for Thanksgiving, they barely concealed their disdain. They didn’t want their daughter to marry someone who, to them, looked like a poor junior science major.
They were polite but clearly disapproved. Eddy, on the other hand, was overjoyed and insisted on inviting Will and me to spend Christmas with his family. My son later told me that his fiancée’s parents weren’t thrilled with our invitation.
An unhappy elderly couple | Source: Midjourney
They smiled and accepted our visit, but secretly began making their own plans.
I decided to play the game.
We took a Greyhound bus to their beach house in Narragansett, and I dressed in secondhand clothes from charities. When Farlow picked us up at the bus station, that’s when it all began…
A father and son at the bus station | Source: Midjourney
He examined me as if I were homeless.
Throughout the visit, he bragged about his wealth, clearly trying to make me feel small.
But I kept quiet, even when they gave Will a brand-new Porsche as an early wedding present on Christmas Eve. Farlow’s smug look told me he thought he’d won.
“Well, Eddy,” I said, pulling out an envelope, “Will told me you’re planning on moving to New York. I hope this helps.”
A man delivering an envelope | Source: Midjourney
Farlow scoffed. “What’s this? A list of shelters in Manhattan?”
Eddy opened the envelope and jumped when he looked at the documents inside.
“Sam… is this true?”
Will rushed over to hug me, and Eddy turned to his parents.
“Sam gave us the deed to a house in Tribeca.”
Marta and Farlow were stunned.
“But… you’re poor…” Farlow stammered.
I smiled. “I wanted my son to be loved for who he is, not for the $570 million he’ll inherit.”
A father and son embrace | Source: Midjourney
After that, there were no more objections, as Farlow and his wife became Will’s biggest fans. My son and Eddy got married that summer. And when they had their daughter, Rain, three years later, I bought the house next door to be close to them and help with my adorable granddaughter.
2. I thought I was marrying the man of my dreams until I saw his true character in the face of poverty
When my parents first introduced me to Walter, I wasn’t exactly thrilled with the idea of a blind date. But when I saw him for the first time, I gasped. He stood up, dressed in a clean suit, his blue eyes sparkling in the dimly lit restaurant.
A well-dressed man in a restaurant | Source: Midjourney
He greeted me with a warm smile and helped me sit down, which made my heart skip a beat.
“Ava, this is Walter,” her mother said proudly.
My mother, Hilda, nudged me with her elbow and whispered, “What do you think?”, noticing the blush rising on my face.
I wasn’t very excited about the meeting, but Walter quickly won me over. Throughout the evening, he was kind, attentive, and everything I hadn’t expected!
A happy woman at a restaurant | Source: Pexels
When he proposed to me a few weeks later, getting down on one knee with a diamond ring, I didn’t hesitate!
“I’ll marry you!” I said with a smile, and the deal was sealed.
We were supposed to get married in a week, and my parents were literally crazy about him!
As the wedding approaches, I couldn’t have been happier!
One day, while shopping for my wedding dress with my friend Hillary, I heard some women talking in the store. What they said left me speechless…
Two women talking | Source: Unsplash
“Did you hear that Walter, the blue-eyed playboy, is getting married?” one of them whispered.
“I heard his parents found him a millionaire’s daughter,” the other added with a chuckle.
At first, I lost interest. There were many Walters in the world, and I refused to believe that my Walter could be the subject of their gossip. Yet, doubts began to creep in.
Later that day, I went to Walter’s house. The rain had flooded the streets, and as I passed a group of homeless people, I heard one of them say, “That rich guy in the red car sprayed us with water. It’s not even his money, it’s his parents’.”
Disgruntled homeless people | Source: Midjourney
These words hit me hard…
Could they be talking about Walter? I didn’t want to believe it. But as I pulled into his driveway, I heard him screaming inside.
“Get them out of here! I want them gone!” he barked into the phone.
When he saw me, his voice instantly softened.
“I just wanted to make sure the homeless had shelter in this rain,” he explained.
I wanted to believe it, but something didn’t add up.
A suspicious woman | Source: Midjourney
I mean, he’s a really good person, really, but I started to get the feeling that he wasn’t exactly who he seemed. That night, I couldn’t stop thinking about it, so I called Hillary and we came up with a plan.
“I have to see who Walter really is,” I told him.
To check, I spent a few days with him, and he was his usual Mr. Generosity, especially in public. But I wouldn’t know who he really is if I didn’t go to extremes, and that’s when things got interesting…
A happy couple | Source: Pexels
Instead of hiring a private investigator to find out the truth, I decided to test it myself.
The next day, I hired an actor, Joe, to pose as a homeless person at Walter’s favorite coffee shop. I wanted to see how my fiancé would react to someone less fortunate. Hillary and I sat, hidden and disguised with large hats, in a corner, watching intently.
At first, he seemed generous, paying for the man’s meal. But then Joe “accidentally” spilled coffee on Walter’s expensive sweater. My fiancé’s face turned red, and although he smiled, he said, “It’s no big deal.”
A man with a stain on his hoodie | Source: Midjourney
What I didn’t realize was that he had spotted me and knew I was watching him, so he pretended to be a nice person. After we left the cafe, Walter, who had brought Joe another cup of coffee, led him outside.
But once they were out of sight, he grabbed him by the shirt!
“If you say anything to Ava, you’ll regret it,” he hissed, before throwing his coffee at the man and storming off.
Fearing for his life, Joe ran away and didn’t bother to contact me again to give me his opinion, which led me to believe that Walter was indeed a good man.
A stressed homeless man | Source: Freepik
But a few days later, two women approached me in a shop. One of them looked at me seriously and asked, “Are you the woman who is going to marry Walter?”
Confused and thinking she was one of Walter’s exes, I replied, “Yes, I am, and I’m doing it because I love him. What does that matter to you?”
“Don’t marry him. He’s not who you think he is,” she said before storming off with her friend.
Alarmed, I hesitated to follow them, and by the time I acted, they were gone. So I brushed it off, but I couldn’t shake the feeling that something was seriously wrong.
A woman standing on the street | Source: Pexels
Unfortunately, this nagging feeling refused to go away, and I decided to test Walter one last time, alone this time. The horror began when he arrived at the fancy restaurant where we were supposed to meet. He found me waiting for him at the door, disguised as a homeless person.
When I approached him begging, he gave me a smile I didn’t realize was fake, but he barely acknowledged me. He reluctantly handed me some money before walking away.
Man gives money to homeless woman | Source: Midjourney
Seeing his kindness, I felt guilty for not trusting him and decided to follow him inside to apologize, where there was no one there except for a waiter. Everything changed when I tried to grab his arm. Just as I was about to shout his name, he turned around and slapped me!
“I… I’m a woman,” I stammered in shock as Walter gave me a hostile, unfamiliar look.
“You filthy witch! The only reason I didn’t slap you before was because we were in public. How dare you follow me!” Walter yelled. “Poor beggars, you’re the ones I hate the most!”
An angry man shouting | Source: Midjourney
When I revealed myself, Walter’s face went pale. “Ava? What are you doing?” he stammered.
“I see you as you really are now, Walter,” I said, feeling the weight of my decision lift from my shoulders. “The wedding is off.”
Months later, my parents introduced me to another potential partner, Brandon. He seemed polite, charming, and well-mannered. But I knew it was better now.
When he smiled and introduced himself, I smiled back, already planning how I was going to deal with him. I wasn’t going to be fooled again.
A woman smiling on a date | Source: Pexels
3. When I asked the girl of my dreams to live in a shabby house, she showed me her true colors.
I grew up in a home that was more miserable than anything else. My mother married my father for his money, and once she had me, she considered her duty done. I saw how heartbroken my father was, knowing that the woman he loved didn’t care about him.
A couple shown separately | Source: Pexels
She lived for luxury and status while he lived for love, and I swore that would never be my life. I would never marry a gold digger, no matter what.
After studying abroad for years, first in England and then in Australia, I returned home with almost no connection to my community. My mother had remarried and never contacted me, and I only had my father and grandmother, which was fine with me.
No one here knew I was the son of Danton Hardy, the heir to Hardy Industries, and I wanted to keep it that way.
A young man | Source: Unsplash
“Dad, I was thinking,” I said one night, “what if I started working in the company?”
Dad lit up. “That’s great! You can start as VP of Marketing!”
But I shook my head. “No, I want to start at the bottom and work my way up. Don’t tell anyone who I am. Hire me as an intern.”
He looked skeptical. “You know the pay isn’t great, right?”
I laughed. “It’s okay, I can live at home.”
A father and son talking | Source: Midjourney
So I bought a modest used car, got some thrift store clothes, and started as a marketing intern. I loved it! I made friends, including Cynthia, another intern, who quickly became my best friend.
One day I was jogging and walked past a Starbucks when a girl came out and ran into me! Her coffee flew out and soaked me.
“Oh my God, I’m so sorry!” she said, her eyes wide.
“It’s okay,” I stammered, completely stunned… she was the most beautiful girl I had ever seen.
A shocked woman | Source: Midjourney
“Is everything okay?” she asked, worried.
I rushed to say to him: “Please have a coffee with me?”
Her name was Linda, and she accepted my proposal. From that moment on, I was hooked! We started dating, and I fell in love! I thought she was the one and even told my grandmother, but she was skeptical.
“My dear,” she said, “a pretty face does not always mean a good heart.”
“Grandma,” I insisted, “she doesn’t know I’m rich. She thinks I’m just an intern.”
“And you don’t know who she really is either,” she warned, but I was too far away to hear her.
A man talking to his grandmother | Source: Midjourney
Even Cynthia was suspicious.
“I went to high school with Linda,” she once said. “She’s beautiful… and quite ambitious.”
I pushed her away. “Me too!”
But her words lingered, and I decided to test Linda. I bought a modest but stunning five-carat diamond and rented a shabby house in a poor but respectable neighborhood. I filled it with candles and rose petals, creating the perfect scene for a marriage proposal.
I called her to tell her I had a surprise and when I brought her home, her face contorted in disgust.
Even when I knelt down and held out the ring, she couldn’t hide her disdain.
A man proposing marriage | Source: Unsplash
Despite everything, I went ahead with my plan, telling her, “Linda, I love you. I want to spend the rest of my life with you. Will you marry me?”
She looked around in disbelief.
“Marry you? Are you serious?”
“Completely,” I said, smiling.
She scoffed. “You think I’m going to live in this dump? And that ring, is it fake? I deserve better than that, better than you!” Then she left, leaving me devastated.
A distraught woman leaving a shabby house | Source: Midjourney
The next few days were a blur. I barely spoke to anyone, but Cynthia noticed.
“Andrew,” she said softly, “she’s not worth it.”
“What do you mean?” I asked.
“I didn’t mean to hurt your feelings, but Linda always said she’d marry a rich man. She was leading you on, Andrew.”
I broke down. “I got angry. You think you know me? You don’t!”
Cynthia turned pale and left the office, and as soon as she was gone, I regretted it.
An upset woman walking away | Source: Midjourney
I called and texted her, but she didn’t respond. I inquired and learned that she had requested a transfer to another department! I realized then how much I had hurt my only true friend.
Over the next few weeks, I missed her more and more. I thought about our friendship, her honesty and kindness. I knew I had to make things right. So I showed up at her door, my heart pounding, and knocked.
A man holding flowers in front of an apartment door | Source: Midjourney
When she opened it, I held out the flowers.
“I’m sorry, Cynthia. Please forgive me. Be my friend again.”
She shook her head.
“No, Andrew. I can’t. I realized when you started seeing Linda that I’m in love with you.”
Before she could say another word, I pulled her into my arms and kissed her.
A man and a woman kiss | Source: Midjourney
A year later, Cynthia and I got married. Linda, on the other hand, was shocked when she saw the news. “Industrial heir Hardy marries in romantic ceremony” was the headline. After all, she hadn’t found her millionaire.
A shocked woman watching the news | Source: Midjourney
Read also: A disabled homeless man gave his wheelchair to a poor boy who couldn’t walk – 5 years later, the boy found it to repay his kindness
This work is inspired by real events and people, but has been fictionalized for creative purposes. Names, characters, and details have been changed to protect privacy and enhance the story. Any resemblance to real persons, living or dead, or to actual events is purely coincidental and not intended by the author.
The author and publisher make no claims regarding the accuracy of events or character portrayals and are not responsible for any misinterpretations. This story is provided “as is,” and all opinions expressed are those of the characters and do not reflect the opinions of the author or publisher.
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