Sometimes people have to go to extremes to attract the right people, and that is the case in the following stories. The wealthy characters in these tales donned cheap clothes, begged, and even pretended to be homeless to see the truest nature of those close to them, and the results were astonishing!

In the following tales, our protagonists face pompous rich parents who think their daughters deserve rich suitors or nothing less, wealthy men who pretend to be good people to snag the richest girls, and girlfriends who only want to marry well-off men. Let’s delve in:

1. My Son Wasn’t Good Enough for His Fiancée’s Parents Until They Discovered the Truth About Him

When I, Sam Sutton, invented an unbreakable engine sealant, I never imagined it would someday impact my son Will’s love life. The money poured in, changing things dramatically for us, but I soon learned that money couldn’t buy everything.

There are two things in life that money can’t buy: love and good health. I found out about the first in the most painful way when my wife, Rain, passed away despite all the wealth in the world, and I learned about the second when Will grew up.

I was left to raise my only child and son as a single father, and I made some mistakes along the way, like spoiling him. But he grew up kind, loving, and unspoiled. In high school, he became popular, though it was obvious that people were drawn to him not for his character, good looks, or kindness, but for my money.

The girls were particularly interested in him, but Will quickly realized they weren’t keen on HIM; they wanted the trips, the luxury, the lifestyle. One night, he came to me heartbroken.

“Dad, the girl I love only cares about the money.”

“Then let her go, my son,” I said, hating to see him so hurt.

After that, Will kept his distance from shallow friendships.

Then, one evening, 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?”

“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 got him scruffy, second-hand clothes, and he went to Yale looking like he didn’t have a penny to his name! The plan worked perfectly! Will made true friends and met a girl he genuinely liked, Edwina, or Eddy, as she was known.

By his third year, my son was in love and ready to propose! I was concerned he might be too young, but he was sure. Eddy said yes, and everything seemed perfect… until he met her parents, Marta and Farlow.

They were wealthy, proud, and deeply unimpressed with Will. When he visited them for Thanksgiving, they barely hid their disdain. They didn’t want their daughter to marry someone who, to them, looked like a poor third-year science major.

They were polite but clearly disapproved. Eddy, however, was head over heels and insisted on inviting Will and me to spend Christmas with her family. I later heard from my son that his fiancée’s parents weren’t thrilled about our invitation.

They smiled and agreed to our visit, but they secretly started making plans of their own.

I decided to play along with the act.

We took a Greyhound bus to their beach house in Narragansett, and I dressed in old, second-hand clothes from the Goodwill. When Farlow picked us up from the bus terminal, that’s when the real fun began…

He looked me over like I was a homeless man.

Throughout the visit, he boasted about his wealth, clearly trying to make me feel small.

But I kept quiet, even as they handed 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 mentioned you two plan to move to New York. I hope this helps.”

Farlow scoffed. “What’s that? A list of shelters in Manhattan?”

Eddy opened the envelope and gasped while looking at the paperwork inside.

“Sam… is this real?”

Will rushed over to hug me, and Eddy turned to her parents.

“Sam’s given us the deed to a brownstone 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.”

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 lovely granddaughter.

2. I Thought I Was Marrying the Man of My Dreams Until I Saw His Real Character When Faced with Poverty

When my parents first introduced me to Walter, I wasn’t exactly thrilled about the idea of an arranged meeting. But when I saw him for the first time, my breath caught. He stood up, dressed in an immaculate suit, his blue eyes sparkling in the dimly lit restaurant.

He greeted me with a warm smile and helped me into my seat, making my heart skip a beat.

“Ava, this is Walter,” his mother said proudly.

My mom, Hilda, nudged me and whispered, “What do you think?” noticing the blush creeping up my face.

I hadn’t been excited about this meeting, but Walter quickly won me over. Throughout the evening, he was kind, attentive, and everything I hadn’t expected!

By the time he proposed a few weeks later, going down on one knee with a diamond ring, I didn’t hesitate!

“I’ll marry you!” I said with a grin, and the deal was sealed.

We were supposed to get married in a week, plus my parents were literally crazy about him!

As the wedding approached, I couldn’t have been happier!

One day, while shopping for my wedding dress with my friend Hillary, I overheard some women talking in the boutique. What they said left me reeling…

“Did you hear 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 as they chuckled.

At first, I brushed it off. There were plenty of Walters in the world, and I refused to believe my Walter could be the subject of their gossip. Still, the doubts began creeping in.

Later that day, I drove to Walter’s house. The rain had soaked the streets, and as I passed a group of homeless people, I overheard one of them say, “That rich guy in the red car splashed water on us. It’s not even his money; it’s his parents.”

The 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 shouting inside.

“Get them out of here! I want them gone!” he barked into the phone.

When he saw me, his voice softened instantly.

“I was just making sure some homeless folks had shelter in this rain,” he explained.

I wanted to believe him, but something didn’t feel right.

I mean, he’s really a good person, really, but I started feeling like he’s not exactly what he seemed. That night, I couldn’t stop thinking about it, so I called Hillary and we devised a plan.

“I need to see who Walter really is,” I told her.

To check, I spent a couple of days with him, and he was Mr. Generosity himself, especially in public. But I wouldn’t be who I am if I didn’t go to extremes, and that’s when things got interesting…

Instead of hiring a private investigator to find out the truth, I decided to test him myself.

The next day, I hired an actor, Joe, to pose as a homeless man at Walter’s favorite café. I wanted to see how my fiancé would react when faced with someone less fortunate. Hillary and I sat hidden and disguised in big hats in a corner, watching closely.

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 though he smiled and said, “It’s no big deal.”

What I didn’t realize was that he’d spotted me, and knew I was on to him, so he pretended to be a good person. After leaving the café, Walter, who’d gotten Joe another cup of coffee, led him outside.

But once they were out of view, he grabbed him by the shirt!

“If you say anything to Ava, you’ll regret it,” he hissed, before tossing his coffee at the man and storming off.

Fearing for his life, Joe ran away and didn’t bother getting back to me to give me feedback, so I was left to believe that Walter was indeed a good man.

But a few days later, two women approached me at a boutique. One of them looked at me seriously and asked, “Are you the woman who’s marrying 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 is it to you?”

“Don’t marry him. He’s not who you think he is,” she said before she and her friend stormed off.

Alarmed, I hesitated to follow them, and by the time I acted, they were gone. So, I brushed it off but couldn’t shake the feeling that something was deeply wrong.

Sadly, that niggling feeling refused to go away, and I decided to test Walter one last time, this time by myself. The horror started when he arrived at the fancy restaurant where we were supposed to meet. He found me waiting outside for him at the door, disguised as a homeless woman.

When I approached him begging, he gave a smile I didn’t know was fake but barely acknowledged me. He grudgingly handed me some money before walking away.

Seeing how kind he was, I felt guilty for not trusting him and decided to follow him inside to apologize, where no one was around except one waiter. Everything changed when I tried to grab his arm. As I was about to call out his name, he turned around and slapped me!

“I… I’m a woman,” I stuttered in shock as I watched Walter glare at me with hostile, unfamiliar eyes.

“You stinking witch! The only reason I didn’t slap you before was that we were in public. How dare you follow me!” Walter yelled. “You poverty-stricken set of beggars, I hate your kind the most!”

When I revealed myself, Walter’s face turned pale. “Ava? What are you doing?” he stammered.

“I see you for who you really are now, Walter,” I said, feeling the weight of my decision lift off my shoulders. “The wedding is off.”

Months later, my parents introduced me to another potential match, Brandon. He seemed polished, charming, and well-mannered. But I knew better now.

As he smiled and introduced himself, I smiled back, already plotting how I’d handle this one. I wasn’t going to be fooled again.

3. When I Proposed to the Girl of My Dreams in a Shabby House She Showed Me Her True Colors

I grew up in a house that was more miserable than anything. My mother married my father for his money, and once she had me, she considered her duty done. I saw how heartbroken my dad was, knowing the woman he loved didn’t care about him.

She lived for luxury and status while he lived for love, and I swore that would never be my life. I’d never marry a gold digger, no matter what.

After studying abroad for years, first in England and then Australia, I came home with almost no ties to my community. My mom had remarried and never contacted me, and I had just my dad and grandmother, which was fine by me.

Nobody here knew I was Danton Hardy’s son, heir to Hardy Industries, and I wanted to keep it that way.

“Dad, I was thinking,” I said one night, “how about I start working at the company?”

Dad lit up. “That’s great! You can start as vice president of marketing!”

But I shook my head. “No, I want to start at the bottom, work my way up. Don’t tell anyone who I am. Just hire me as an intern.”

He looked skeptical. “You know the pay’s not great, right?”

I laughed. “That’s fine, I can live at home.”

So, I bought a modest second-hand car, got a few 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 ran past a Starbucks when a girl came out and slammed right into me! Her coffee went flying, drenching me.

“Oh my God, I’m so sorry!” she said, wide-eyed.

“It’s okay,” I stammered, completely stunned… she was the most beautiful girl I’d ever seen.

“Are you alright?” she asked, concerned.

I blurted out, “Please, have coffee with me?”

Her name was Linda, and she agreed to my proposal. From that moment, I was hooked! We started dating, and I fell hard! I thought she was the one and even told my grandmother, but she was skeptical.

“Sweetheart,” she said, “a pretty face doesn’t always mean a good heart.”

“Gran,” 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 gone to listen.

Even Cynthia was wary.

“I went to high school with Linda,” she said one day. “She’s beautiful… and quite ambitious.”

I brushed her off. “So am I!”

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, setting the perfect scene for a proposal.

I called her and told her I had a surprise and when I brought her to the house, her face twisted in disgust.

Even as I got down on one knee and held out the ring, she couldn’t hide her disdain.

Still, I proceeded with my plan saying, “Linda, I love you. I want to spend the rest of my life with you. Will you marry me?”

She looked around, incredulous.

“Marry you? Are you serious?”

“Completely,” I said, smiling.

She scoffed. “You think I’d live in this dump? And that ring, what is it, fake? I deserve better than this, better than you!” Then, she walked out, leaving me crushed.

The next few days were a blur. I barely spoke to anyone, but Cynthia noticed.

“Andrew,” she said gently, “she’s not worth it.”

“What do you mean?” I asked.

“I didn’t want to hurt you, but Linda always said she’d marry rich. She was leading you on, Andrew.”

I snapped. “Shut up! You think you know me? You don’t!”

Cynthia paled and left the office, and as soon as she was gone, I regretted it.

I called her and sent texts, but she didn’t respond. I asked around, only to find out she’d requested a transfer to another department! I realized then how badly 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 her kindness. I knew I had to make things right. So I showed up at her door, heart pounding, and knocked.

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 year later, Cynthia and I were married. Linda, meanwhile, got a shock when she saw the news. “Hardy Industry Heir Marries in Romantic Ceremony” was the headline. She’d missed out on her millionaire after all.

If you enjoyed those stories, then you’ll love this one about a man who was once rich but lost everything due to marrying the wrong person. The man attended his ex-wife’s wedding to another wealthy unsuspecting victim as a homeless man, trying to save the new guy from the same heartache he’d faced.

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.