homeless man
Jade Small
Jade Small
February 24, 2023 ·  5 min read

Rich Girl Meets Homeless Ex. What Boyfriend Tries To Do Is Despicable – a Short Story

Mary was born into wealth. Her father owned a large corporation that set his family into a life of lavishness. Most people would assume they are snobs but, in reality, they were kind-hearted. They did not let the money get to their heads, which is what happens to so many people. In high school, she was known for her generosity. This was the quality that attracted her first boyfriend, Matt.

The years after graduation

When it came close to the time they would graduate, Mar and Matt had to have that difficult conversation about what would happen to their relationship. Matt wanted to try long-distance dating, as Mary had been accepted to a university in another state. However, as time went on, they grew apart. This was heartbreaking for Matt, but he knew he had to let her go for her to flourish.

A few years later, Mary visited her father at work. It was his birthday, and she would take him out for lunch. When she arrived, there was another man in the office. Her father introduced him as one of his brightest interns. He had shown such promise that he offered Petter a full-time contract. Mary was extremely attracted to Peter. So, when her father asked if he could join them for their lunch date, she could barely refuse.

MAry came to visit her father at work, and there she met Peter.
Image credit: Pexels

They hit it off right away, and Mary found herself falling for Peter much quicker than she ever thought possible. They dated for a few months, and everything seemed like a fairytale. One evening, he took her out for dinner. Everything was so romantic.

He had booked a private section at an Italian restaurant. There were roses everywhere, which he boasted about. He thought they were her favorite flower. But, in actuality, she preferred orchids. However, Peter got down on one knee at the night’s end and proposed. Mary forgot bout the flowers and immediately said yes.

Six months later

Six months later, the wedding plans were well underway. Mary and Peter were walking down the street one day don’t their way to see the wedding planner. On the way, she tripped over a homeless man’s foot. She did not see him sitting there. Peter yelled at the man, but Mary raised her hand to stop him. She apologized to the homeless man. He looked up, surprised, and she immediately recognized him. It was Matt, her first boyfriend from high school.

Her ex was there living on the streets
Image credit: pexels

Peter was shocked when he realized they knew each other. He stood there with his mouth open while Mary and Matt caught up. When they finally moved along, Peter realized his wallet was missing. He immediately threw accusations that Matt, the homeless man, had stolen it. Mary refused to believe it. Next thing, Matt came running down the street shouting that Peter had dropped his wallet while they were talking. Mary looked at Matt, with eyes that said, “I told you so.

She gave him a job

Mary decided to help her ex-boyfriend. She spoke to her father, and he gave Matt a job at his company. Peter was very jealous, but he was most suspicious of Matt. One day, Matt was walking past Peter’s office and heard a woman’s laugh coming from inside.

The blinds had been drawn shut, but he could see through a little gap. The woman was sitting on Peter’s desk, she was definitely flirting. Peter tried to assume that she was trying her luck and Peter was being targeted. But the next thing Matt saw was Peter grabbing her face, and they started kissing.

When Peter and the woman left the office, he heard them talking about a locked drawer in Peter’s desk. He had been doing shady deals, which he kept a secret from Mary’s father. Furthermore, he heard even more shocking news. Peter was only marrying Mary to gain access to her trust fund. The worst part was they planned to kill Mary the moment he had control of her money.

Matt peeked through the blinds of Peter's office
Image credit: Pexels

Matt could not believe what he had just overheard. He absolutely could not let this happen. When everyone at the office had gone home, he broke into Peter’s office. He wanted to find the key to the locked drawer so he could prove to Mary what peter’s true intentions were.

They caught the wrong man

When Peter came to work the next day, he did not expect to see Mary and Matt waiting in his office for him. Mary had a very serious expression on her face. When Peter asked her what was happening, she said, “I could ask you the same thing.”

Peter looked at Mary questioningly. Mary sighed and said Matt had told her about the woman in his office. Peter looked surprised, and he threw Matt a menacing glare. He flat-out denied the accusation that he was chatting on Mary.

Instead, he accused Matt of stealing money from his office drawers. He said he noticed Matt peeking through his blinds the day before while he was stashing an envelope in his drawers. Matt protested. He said he knew nothing about the money. So, Peter suggested they search all the employee’s lockers – starting with Matt’s.

Mary agreed, and they went straight to open the locker. Lo and behold, there was an envelope right in front, at eye level. Mary looked at Matt with disappointment. Matt tried to explain that someone was setting him up. He had no idea where the money came from. Mary sighed and told Matt to leave. Peter looked smug. He watched as Matt left the room to collect his things.

The truth comes out

That evening, Peter was going to his car when Matt jumped out from behind a pillar. He had been waiting in the parking lot for Peter to finish work so he could corner him. He accused Peter of cheating. He also explained that he heard his and his girlfriend’s plans to kill Mary when he accessed her trust fund. Peter laughed.

Mary was furious when she found out the truth
Image credit: Pexels


With an evil look on his face, he admitted to everything. He explained it all in detail and said that no one would ever believe Matt now as he was a proven thief who used to be homeless. Then, suddenly, a voice came from around another pillar. Peter’s face froze.

He didn’t realize that Mary was waiting there. She held up her phone and revealed that she recorded his entire confession. It turns out that she chose to believe Matt, even though the odds were against him. This was their plan to fool him into confessing.

The moral of the story is one cannot judge a book by its cover. Just because someone has endured a rough life that left them homeless does not make them a bad person. Sometimes the real evil is right under your nose. You have to use your discernment over the people you wish to keep close to you.

Keep Reading: Kindness Shown by a Man is Just Amazing to Watch – a Short Story

This fictional story was inspired by stories from around the web. Any similarities between this story and actual people are purely coincidental.