Jade Small
Jade Small
May 12, 2024 ·  6 min read

Homeless Young Woman Marries Old Man without Knowing He Is a Millionaire – a Short Story

More often than not, forgiveness is the answer. If you can forgive someone for something they have done to you, you can move on with your life. It is those who have wronged us or treated us poorly who will have to live with their wrong-doings. And, that is exactly what this woman learned.

A lonely man

Connor Shaw was a 75-year-old man. While Connor was quite wealthy, he did not share his life with anyone special. Not since that fateful day all those years ago. You see, when Connor was 40, he was married. But, his wife had lost her life in a car accident. Unfortunately, Connor blamed himself for what happened and had been unable to move on with his life.

Connor was so upset and depressed about the accident that he even sent his children, Racheal and Mark, to live in a boarding house for the rest of their school careers – they just reminded him too much of Charlie, his wife, and their mother. Connor knew he was to blame for that accident because he insisted on driving after a work function, even though he was clearly exhausted and a little drunk.

Slowly, Connor only cared for his work, which eventually made him millions. But still, Connor was not a happy man. And even though he was so wealthy, he lived a simple life in a modest home. He did in fact own some substantial property, but he never cared to live there.

No Children to love

While Connor had been the one to send his children to boarding school, they chose to ignore their father after leaving school. Both of his kids attended universities and never really came to visit him. When Connor was 55 years old, he suffered a heart attack and had to be admitted to hospital for two long weeks. Not even a phone call came from either of his children.

All the two children cared for was money from their father, but not the slightest ounce of care was ever extended to him. Connor never felt more alone, he longed for his children and a woman to love and hold as he grew old.

Man in White Thobe Sitting on Bed

A Homeless Lady

Now, at the ripe old age of 75, Connor had given up on finding love again. He had no idea how wrong he was thinking that! One day, Connor went on a morning walk and stopped at a coffee shop to grab a cup of warm coffee. Connor walked out of the store and noticed a woman sleeping in the corner on the sidewalk. She was curled up on a cardboard box. Next to her a sign stood propped up, it read: Homeless and Hungry. Looking for Work. Please Help.

Jacob never really noticed any homeless people asking for a job, usually, all they asked for was money and occasionally food. Jacob decided to approach the woman, he startled her when he spoke and she woke up, but he assured her he wanted to help. Her name was Kayla. He told her that he was looking for a housekeeper, and asked if she would like to try out for the job.

Kayla looked surprised. Connor suggested they talk and get to know one another, he bought her a cup of coffee and the pair sat down at a table inside the coffee store.

The Sad Reality

Connor asked Kayla how she had come to be homeless. With tears in her eyes, she told him how her husband had left her with unimaginable bills. He had left her for another, younger woman. She was also unable to have children, which had angered her husband even more. Connor was heartbroken, and after a few hours of chatting, he eventually offered Kayla a place to spend the night, to which she eventually agreed. She was to start work the very next day. Kayla could not believe her luck.

Connor did not realize it at that moment but he had fallen in love with Kayla at the moment they met eyes. They were the same color as his wife’s eyes had been, and her ash blonde hair was similar too. Kayla made Connor feel like he was no longer alone. He just did not see it yet.

They walked to Connors’s house and he showed her the guest bedroom. He told Kayla to make herself at home, and they agreed that she would start work the next morning at 8 am. Kayla thanked Connor repeatedly for his kindness.

A Year Goes By

A year had passed and Kayla never left the house, the guest bedroom had become her own. She loved living with Connor and looking after him, cooking his meals especially. The pair eventually grew closer and one day, Connor asked Kayla to be his wife.

Cheerful elderly man and adult woman cuddling on white background and looking at camera

Kayla had no idea how wealthy Connor was. She said yes. The couple got married quite soon after. Just the two of them. Of course, Connors’s children did not attend the small ceremony.

One day, the kids wrote a letter to Kayla. They were horrible to her, calling her a gold digger and saying she only married their father for his money. Kayla did not really understand why they would say that, after all, her husband was a simple man. Nonetheless, she loved Connor and did not allow the children’s harsh words to hurt her. Connor insisted they never speak of his children again, and while she did not understand why, she left it at that.

Woman Wearing Wedding Band

An Illness

Ten years had passed, and Connor was frail in his old age. Now 85 years old, he had been sadly diagnosed with Cancer. He would not live long. Soon, the day arrived when Connor did not wake up. Kayla was heart broken, she had lost the only kind person in her life. The man who saved her and helped her. She did not know what she would do without him.

A week passed and Kayla received a call from Connors lawyer. They set up a meeting. Kayla expected to hear about some bills that needed paying, and thought about how she could sell the house if the bills were large. She met with the lawyer and the words he spoke were the last thing she ever imagined. Connor had left her millions, and, his entire estate. Not only did she have no idea that he had any money, but she was now rich herself.

Connors’s children were also at the lawyer’s office for that talk. They were both extremely angry and upset. They were practically ready to rip Kayla apart, yet she had had no idea of Connors’s wealth.

Connor had also left Kayla a letter, explaining in detail why he did what he did. Her heart burst and she broke down in tears as she read how much he loved her.


Even though she had no reason to, Kayla chose to gift Connors children each with a home from his estate. It was her way of forgiving them for what they had done to her, and to their father. She also decided to donate money to the homeless. Because Connor had helped her, she decided to help others.

This story was inspired by an original piece of fiction. Any similarities between this story and actual people is purely coincidental.

Keep Reading: Woman Captures Homeless People for 10 Years and Recognizes Lost Dad in One of the Photos – a Short Story