Homeless Young Woman Marries Old Man without Knowing He Is a Millionaire — Story of the Day

A homeless woman’s life takes an unexpected turn when an old man asks her hand in marriage, and she nods a yes – but the woman has no idea how wealthy her future husband is.

Jacob Conner was 76, insanely rich, but single. No, Jacob had not been a single man his entire life; it was just that fate had not been kind to the man in terms of his love life.

When Jacob was 34, his beloved wife Linda had passed away in a car accident. They were returning from a family event when the accident occurred. Jacob was lucky and he survived, but Linda bled to death even before she could make it to the hospital.

Jacob came across a homeless woman on his way to a cafe one day | Photo: Shutterstock

That fateful day, Jacob was the one behind the wheel. He was exhausted after the function, and Linda had asked him not to drive, but the man insisted, so she gave in. Unfortunately, he dozed off for a second as they were taking a turn near a highway, and their car collided with a truck.

Fast forward 42 years from that fateful day, and Jacob was still not over it. He couldn’t remember a single day when he didn’t regret not listening to Linda and insisting on driving that evening. In fact, after that incident, he had sent his children, Myra and Chris, to boarding schools because they reminded him so much of Linda.

And after the kids left, he immersed himself in work to alleviate his loneliness. He spent several years on his small clothing business, which eventually grew into a well-known brand that earned him millions.

But despite all the money, Jacob always lived a simple life in a typical American home, and the massive villas he purchased were still awaiting its residents.

Jacob lived a modest life in a simple house in New York | Photo: Pexels

Another unfortunate aspect of Jacob’s life was that when both of his children were accepted into prestigious universities, they almost severed their ties with their father and did not visit him for years. All they wanted from Jacob was money, which he never refused to give them. But as far as spending time with their father was concerned, the kids had no interest in it.

For instance, one fateful day after dinner, Jacob had just gotten up from the dining table when he suffered a heart attack. Fortunately, he was at his neighbor’s house for dinner that night, so he was rushed to the hospital right away.

But even after spending 2 weeks there, neither of his children visited him. His son said he was busy on a university trip, while his daughter didn’t even bother to respond to his calls. 

Jacob eventually recovered and returned home, but it was the first time in his life that he felt so alone.

Jacob was rushed to the hospital one night | Photo: Pexels

Decades later, 76-year-old Jacob was strolling through a park when he decided to stop at a cafe for a cup of hot Americano. However, the traffic signal turned red just as he was about to cross the street. The cars began to accelerate quickly, and Jacob had to come to a halt at the traffic light.

As he stood there, looking around, his gaze was drawn to a woman at the back of a store, curled up on a carton and sleeping with a bag under her head. There was also a sign beside her that said, “Looking for a job urgently. I’m homeless and in need of funds to support myself.”

The woman’s placard astounded Jacob because he’d seen several homeless people in New York over the years, but one begging for work was certainly unusual.

Jacob decided to approach the young lady and offer her assistance. “Excuse me, miss, are you all right?” he inquired gently, which jolted the woman awake.

“Oh, ye – yes, I am,” she hurriedly said as she stood up. Her name was Ashley Brown.

“It’s all right, relax; I just read your placard and would like to offer you a job. I’m looking for someone to help me around the house, like a housekeeper.”

Jacob fell for Ashley | Photo: Unsplash

“Really?” Ashley’s eyes widened as she received the unexpected offer.

“Yes, but I’d like to learn more about you. Would you like to join me for a cup of coffee? I heard there’s a really good cafe nearby,” Jacob asked.

“Sure, I’d love to,” Ashley replied, and the two went for a walk to a nearby cafe.

On the way, Jacob inquired about Ashley’s life and how she ended up on the streets, to which the woman replied that she was divorced, kicked out by her husband after a miscarriage. She had only moved to New York two years prior and had no friends or relatives whom she could turn to when all of this happened.

“And that’s how I wound up on the streets. Is there anything else you’d like to know?” Ashley asked as she finished.

“No, nothing else,” Jacob replied. “Look, we are here,” he added, pointing to the cafe. 

Ashley smiled and whispered a thank you to him as they went inside. Jacob got them coffee and sandwiches, and they spent the evening together talking about each other. Jacob asked Ashley to start working the next day and even invited her to spend the night at his house, which Ashey was hesitant to accept at first but eventually did.

Ashley eventually accepted Jacob’s offer to stay in his house. | Photo: Unsplash

When Jacob was talking to Ashley that day, he had no idea he’d fallen for her. She had beautiful hazel eyes just like Linda’s, and her partially brown locks, which were untidily scattered across her face, added to her beauty.

As they left the cafe that evening, Jacob couldn’t take his eyes off her. The snow falling around her and her smile whenever a flake landed on her palm reminded him of the young Linda, and the man didn’t even realize love had returned to his life.

“So, Mr. Conner, how much time do we have before we arrive at your house?” she asked, smiling.

“Oh, my house…Oh, I forgot, it was actually…Never mind,” he stuttered as he realized he had reached another neighborhood. He pretended he’d taken a different route and walked home via a different path.

When they arrived home, Jacob asked Ashley to take the guest room and make herself at home. The young woman thanked Jacob for his assistance, and to some extent, she had developed feelings for him too; not in the way Jacob had felt for her, but because of how kind he was.

Ashley and Jacob grew close over time | Photo: Pexels

Over the next year, as Ashley looked after Jacob and his house, she felt she was growing closer to him. Looking back a year, she had been labeled a filthy homeless woman who had been refused a job by almost everyone. But now, looking at herself, she was proud that she didn’t give up and was earning a living for herself.

However, despite staying with Jacob for so long, she had no clue the man was a millionaire. She just assumed he was a kind, elderly man who was lonely after his wife died and his children became preoccupied with their own lives…

In fact, even when Jacob proposed to her and the two married at a church, she didn’t know Jacob was a millionaire. After all, he’d been living such a simple life that she could never guess. 

But Jacob’s reality was almost revealed when his kids paid him a visit one day and discovered their father was married. 

“What did you just say? You’re my dad’s wife?” Chris lashed out at Ashley when she answered the door and introduced herself as Jacob’s wife.

“Yes, Chris,” Ashley replied sternly. “I’m his wife and your stepmother! Is that clear?”

Chris lashed out at Ashley | Photo: Pexels

“Really?” Chris laughed. “You’re a bloody gold digger! You’re here just for his money.”

“I understand how difficult it is for you and Myra to accept me, but you can’t just say things like that,” Ashley warned him.

“Oh really? Did you marry a man who’s way older than you just because you love him? You expect us to believe that?” Myra interrupted her. “Look, miss, whatever your name is, pack your bags and leave as soon as you can.”

“I don’t believe you have the authority to say that,” their father said as he approached them. “This is my home, and she is my wife. So if anyone is leaving, it’ll be you two.”

Myra had just started speaking when Jacob cut her off. “You kids are good for nothing, so leave.”

The kids were saying something, but Jacob didn’t listen to them. He slammed the door on their face and severed all ties with them. They were, after all, only interested in his money.

“But Jacob,” Ashley said. “They are your children. How can you be so stern? Talk to them once at least.”

“Yes, they are my kids, Ashley,” Jacob said. “I know them well.” And that day, he instructed Ashley never to talk about them.

Jacob kicked his kids out of the house | Photo: Pexels

Ashley had a few questions she wanted to be answered that evening. “Why did the kids keep accusing her of being a gold digger? Was Jacob concealing something?” She was puzzled. However, because Jacob was already upset, she decided not to bring up the kids and what they’d said.

But three years later, when Jacob passed away, all her questions were answered. During those years, the man had been gravely ill and had been diagnosed with a terminal illness. Ashley spent her days and nights by her husband’s side, looking after and caring for him, but his children never came to see him.

After dealing with their children’s betrayal yet again and living a remorseful life, scared of leaving his wife in a terrible state, Jacob rewrote his will, which no one was supposed to know until he died. As a result, when the lawyer read Jacob’s will, Ashley froze in place!

“Mrs. Conner,” the lawyer said. “I’d like to inform you that your husband has left you his entire estate, which includes two mansions and a small house in New York.”

“Mansions? And Jacob… what?” Ashley couldn’t believe her ears! She and her husband had lived the most normal life in the most ordinary house in New York, so hearing that from the lawyer shocked her.

“Yes, ma’am,” the lawyer explained. “Mr. Conner has an overseas business which is currently managed by his partners. The man led a simple life, but he owns a multimillion-dollar business. And you’re his only benefactor.”

Jacob’s children, who were also in the lawyer’s office, were enraged. “I was right when I called you a gold digger! You wanted his money! You are a witch!” Myra screamed and stormed out of the office. Chris felt no less than his sister, and before he left, he lashed out at Ashley as well.

Jacob had left his mansions to Ashley | Photo: Pexels

Meanwhile, Ashley’s eyes welled up after learning Jacob had left everything to her. In a letter, he had explained why he did that and had called her the love of his life.

“I always loved you, and I hope you’re happy. Please live your life happily when I’m not around. You loved me even though you knew I wasn’t a millionaire, which convinced me that you should be the heir to my estate,” he’d written at the end of the note.

After reading Jacob’s letter, Ashley decided she wouldn’t let his trust in her go to waste. So the first thing she did with his money was start a chain of shelter homes for the homeless across New York, where they would be trained for jobs and cared for. Then she gave some of her wealth to charity and one of her mansions to Jacob’s children — as a sign that she forgave them and because she believed it was wrong to leave them without anything.

What can we learn from this story?

  • Learn to forgive and forget. Ashley forgave Jacob’s children and moved on in life.
  • Respect and love your parents. Unlike Jacob’s children, who were only interested in their father’s money and never loved him.

If you enjoyed this story, you might like this one about children who attend their mother’s funeral to divide her inheritance and see her eyes open during the ceremony.

This account is inspired by our reader’s story and written by a professional writer. Any resemblance to actual names or locations is purely coincidental. All images are for illustration purposes only. Share your story with us; maybe it will change someone’s life. If you would like to share your story, please send it to info@amomama.com.

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