Secretary Learns Her Rich Boss Lives in Old Trailer near a Cemetery – Story of the Day

Judy was an assistant to Mr. Rollins, a wealthy man who didn't care about others. Judy noticed odd things about him here and there, but it wasn't until she had to follow him home that she discovered a shocking truth about her boss.

"He never talks to anyone and has no tolerance for people who get into personal business," Alexander nodded at Judy, who listened intently but wasn't entirely comfortable with the conversation. She worked for Mr. Rollins – Peter – for two weeks at a decent company.

She made good money, and the people were friendly. His boss was serious and quiet, but he wasn't mean or anything to her. However, she started going to get coffee with some of the other assistants at the company, and they gossiped too much about their superiors. Today, they decided to tell Judy all they knew about her boss, which wasn't much.

"One time, I was helping him because he had yet to hire a new secretary, and I asked about his wife in passing. It was entirely innocent, and he snapped. Snapped! At me. I ran out of there as quickly as I could," Alexander continued.

Therefore, she would have to find out on her own… somehow.

"We don't know much about him or why he would react like that," another colleague, Umma, added. "He's normally quiet unless you're late or have a project. I guess some rich people hate getting personal or dealing with us mortals. But I have a theory that his wife cheated on him…"

The group laughed, not Judy. But she didn't want her work days to be dull, so she smiled politely and noted the tips about asking Mr. Rollins any personal questions.

***

"Where the hell have you people been?" Mr. Rollins yelled at them as they arrived at the office. "GO TO YOUR DESKS! NOW!"

He had never spoken to anyone that way since Judy was hired, but everyone hurried to their desk. She also threw coffee on her white blouse as she reached her cubicle.

"Judy, come in here!" Mr. Rollins called, and she jumped out of her desk.

"Yes, sir?"

"There's a huge project… I need you to take a look at a month's worth of paperwork as quickly as you can. You might have to put it over time. Come on! Hurry!" he said, not giving her anything more, but she grabbed boxes and started sorting.

As she unearthed some papers, he explained better what he needed and continued to give instructions. It wasn't hard for her to handle. Judy was smart, but it was overwhelming and would take a long time. Eventually, she took everything to her cubicle and used her computer to sort appropriately as well.

Without noticing, the office got dark, and people left. Judy's tummy rumbled, and she realized it was already 11 p.m., but she didn't want to leave. She was almost done, so she grabbed another box and continued.

At 3 a.m., a gentle voice startled her concentration. "Judy? What are you doing at this hour?"

"Oh, wow," Judy swiveled in her chair. "Mr. Rollins, you scared me."

"Why did you stay so late? It's 3 a.m.," her boss continued.

"Wow! I didn't notice!" Judy said, just now looking at the clock, and started to grab her things, as her boss went somewhere else in the office.

"Here, have some coffee, so you don't fall asleep on your way home," he offered, putting a cup on her desk.

"Thank you," Judy said, grabbing the drink gratefully.

She looked at her boss as they drank the bitter liquid and realized he was in fresh clothes, so he would probably stay there until the end of the day. But something caught her attention. His fancy shoes were dirtied as if he had stepped on mud or wet grass. It was weird. She had never noticed that before; he was such a well-put-together man.

"Thank you so much for staying here. I should've been clear that it didn't need to be so late," he added suddenly.

"Oh, Mr. Rollins. I completely lost track of time. I really thought I could finish today… well, it's tomorrow now," she laughed awkwardly, which made her boss grin slightly. Suddenly, her cheeks turned red, and her heart started pumping faster.

His smile was beautiful. His eyes crinkled adorably, and he looked so relaxed. Judy was usually into more hipster, rock-type of men, so she had never seen him as handsome. But at that moment, all she thought about was kissing him.

Mr. Rollins wasn't much older than her, although it had always seemed like it in the daylight or when he had a serious/grumpy face while working. But truthfully, he was only seven years older, and now, she wondered about him.

Did he have a family? Was he divorced? Was he married? But she didn't dare ask so directly. Her work friends were gossips, but what they said about asking him personal questions was real.

"Mother-in-law?" Judy repeated. So, he was married.

"Mr. Rollins, what are you doing here so early?" Judy asked suddenly.

Her boss looked at her intently, making her cheeks redden further. But he cleared his throat.

"Go, Judy. Go home. See you tomorrow," he urged kindly, looking down, and she nodded.

"Well, later today, you mean," Judy said jokingly to lighten the strange mood.

"Oh, yeah. Right," he almost grinned, and she left, thinking about this enigma of his shoes and why he came so early to the office. But she couldn't ask anyone in this place. The gossip would amplify, and Judy didn't want to spread anything about her employer.

Therefore, she would have to find out on her own… somehow.

***

Judy was dead tired when she returned to the office later that day at her usual arrival time. However, she wanted to finish quickly and avoid staying late again. So, she got down to business. Unfortunately, she couldn't finish all her work that day either and decided to stay a few hours late again.

"Judy, go home," her boss interrupted her. "Now. Thank you for taking this project so seriously, but you can't stay that late again."

"Oh, thank you, Mr. Rollins," Judy said, wrapping up her day. She watched him leave and saw the entire empty floor. She stood, looked at his office to see if there was anything to arrange, and noticed a few snacks and old wrappers from cheap fast food on his desk. She discarded those, unearthing his cell phone.

Judy ran, grabbing her purse on the way to the parking lot. She arrived just in time to see his car exiting, so she ran to hers and followed as quickly as possible. She didn't want him to be without his phone and didn't know who else to call.

However, the road he took was strange, and Judy wondered where exactly he lived. There was a ritzy neighborhood in town, and she thought he would have a house there. But they were going in the opposite direction.

They reached an empty area, and Judy realized they were near the city cemetery. She followed him until he parked beside an old trailer and went inside. He didn't notice another car behind him or the headlights for some reason, but she parked nearby and knocked on the trailer door.

"Judy? What are you doing here?" he asked, his eyes wide and his tone outraged.

"You forgot your phone in the office! I followed you here," Judy said quickly, returning the device to him.

"You shouldn't have come here," he continued, quickly taking the mobile from her hands. "Leave."

"Yes, I will," Judy said, but she took a peak inside the trailer and saw it was dirty and unkempt. It didn't seem like the place for her boss to live in.

"JUDY! LEAVE! NEVER COME BACK HERE!" Mr. Rollins suddenly yelled, and she flinched, backing away to her car quickly. "DON'T TELL ANYONE WHERE I LIVE, ESPECIALLY YOUR STUPID FRIENDS AT THE OFFICE!"

Judy nodded awkwardly as she got into her car and drove off. This was the first time Mr. Rollins had screamed at her in anger, and she felt terrible. However, Judy could barely sleep when she got home, thinking about his living situation.

***

A few days later, they finished everything they needed for the new project, and Mr. Rollins had several meetings with particular clients, so Judy didn't have much to do. She entered his office, threw out more fast food wrappers, and looked around. Suddenly, she saw his keys on the desk and had an idea.

She didn't want to ask Mr. Rollins why he lived in a trailer, considering how much money he earned, why he always ate fast food and unhealthy snacks, or why he came to the office at random hours of the night. But she could do something for him.

Will he fire me? Judy thought as she took the keys to his home and went to grab her purse. Whatever. I'm good. I can find a new job. I need to know more about him.

She knew this situation wouldn't be happening if she had felt her heart beating so fast the other night. She wanted to learn more about him. She needed to do this for him. She needed to find out why he acted a certain way, why he looked like the weight of the world was on his shoulders, why he never smiled, why he was so alone… and so many more things.

She wanted to know all about him, so she drove, went to the supermarket, bought everything she needed, and headed to his trailer. She cleaned up, stored real food in his fridge, and started cooking some things for him, so he would finally have real things to eat at the office.

But the door swung open, and Judy thought he had caught her. Instead, it was an older woman whose eyes widened at her. But her smile lit up the room just as quickly. "Who are you, dear?" she asked, excited for some odd reason.

"Hello, I'm Judy. I'm Mr. Rollins's secretary," she introduced herself, extending her hand.

"He begged me," Mr. Rollins choked a bit on those words.

The older woman's smile disappeared weirdly. "Oh, I see," she said, disappointed. "Well, I see that he at least asked you to clean this place."

"Well, he didn't ask me or knows I'm here," Judy shrugged.

"Really?" her smile appeared again. "I'm Miriam, dear. I was Peter's mother-in-law."

"Mother-in-law?" Judy repeated. So, he was married.

"Yes," she nodded. "You're new?"

"Yeah, I've only been working for him for a few weeks."

"But he must like you if you know where he lives," Miriam tilted her head.

"He didn't tell me. It's a long story," Judy replied.

"We have time," Miriam urged.

Judy laughed and recounted everything. They chuckled some more, and then, she asked. "So, he lives here with his wife?"

"Oh, I should've been clear. My daughter died years ago… with my grandson. They were in a car accident," Miriam revealed, her lips pulling down. "Peter…never recovered. He blames himself, even though he wasn't in that car at all."

"I'm terribly sorry for your loss," Judy said, shocked and dismayed.

"Thank you, dear. Things since then have been a whirlwind. Peter went through intense grief, and we couldn't help him. I mean, my husband and I couldn't do much for him. He was depressed and just went through the motions. He went to work, but life had no more meaning for him," Miriam continued. "Until my husband got sick…"

"Oh no," Judy uttered.

"Yeah. But my husband's sickness snapped Peter out of his depression. He put all his efforts into helping us out. He pays for everything, and at the hospital, he met many sick kids, so he now gives to charity. He sold almost everything he owns and bought this trailer and this piece of land, so he could be near the cemetery where my daughter and grandson are buried," the older woman explained.

"I see."

"But it's not a life," Miriam said, her eyes watering. "Despite all the good he does, he is not living at all. He leaves no money for himself or buys anything, or enjoys anything. I think he only kept his clothes to go to work dressed nicely. We all have told him to move on. It's been years. I know my daughter wouldn't have wanted him to live like this. He doesn't care about himself, and he has insomnia. So, he visits their graves late at night or goes to work."

"Wow. That's terrible," Judy said, realizing why his shoes had been dirty the night he entered the office at 3 a.m. He had just been to his family's graves.

"So, I was excited when I saw you here. I thought he was moving on," Miriam said, grabbing her hand. Judy was confused. "I thought you might be his girlfriend."

"Oh, no, ma'am. I'm just his secretary," Judy shook her head.

"Are you sure?" Miriam asked hopefully, but the door to the trailer swung open again, and Peter stood there. His eyes were big as saucers, and his face turned white as a sheet.

"Judy! WHAT DID I TELL YOU BEFORE?? NEVER COME BACK TO MY HOUSE!" he screamed, more furious than ever, and although Miriam tried to defend her, Judy ran off.

She didn't need his gratitude or anything. She only wanted to do something nice for him, especially after discovering everything about him.

***

The next few days were awkward, but he had not fired her. But one day, he unexpectedly came out of the office with his phone in his ear. "Judy, cancel all my appointments. I have to go to the hospital," he said.

"Are you alright, sir?" she asked.

"Yeah. It's my father-in-law," he answered and walked to the elevator.

Judy canceled everything and finished her work for the day. It wasn't until she got in her car that she realized Mr. Rollins had not snapped or gotten angry at her for her questions. He had actually told her something personal.

Judy took it gratefully and looked down at his shoes. They weren't dirty. He's really moving on.

So, Judy arranged some flowers and sent them to the hospital, hoping his father-in-law was alright.

The next day, Mr. Rollins called her to his office as soon as she arrived, and she was scared until she saw his face. He was peaceful. Something had changed.

"Is everything OK, Mr. Rollins? Were the flowers alright? Is your father-in-law better?" she asked, unable to stop herself.

"Sit down, Judy… please," he said kindly. She did and braced for whatever he wanted to say. She had gotten personal again; maybe, yesterday had been a fluke.

"My father-in-law passed last night," he started. "I'm going to need help to arrange his funeral."

"Sure," Judy said, getting his notepad out.

"But before that," Mr. Rollins stopped her, holding his hand out. "I want to thank you. For the flowers. For cleaning my trailer and making me food. For not telling anyone about this. My other secretaries were just as gossipy as the rest of this office. I appreciate your seriousness and loyalty."

"I'm just doing my job, sir," Judy smiled.

"You do more than that for me. I don't understand why since I haven't been the nicest boss in the world. But you do it," Mr. Rollins continued. "My father-in-law, Roger, thanked me yesterday for everything I did for them and all the good I've done since I lost my wife and son. I know Miriam told you about that."

"Sorry," she said, sheepish.

"It's alright. It's nice that someone knows the truth now. Most people here don't know anything about me except my bosses," he said. "Anyway, Roger told me that I was not living. That I had died with my family that day. And it's true. That's how I felt. But that I needed to start acting alive. I needed to move on. I needed to find someone special."

Judy couldn't nod as her eyes watered.

"He begged me," Mr. Rollins choked a bit on those words. "He pleaded with me to start living again. To date. To make another family because that's what my wife would've wanted. Do you think that's true?"

She didn't know what to say. "That's what Miriam told me, too. That day. They want you to be happy. Or at least, try to be," Judy replied quietly.

Mr. Rollins nodded, thinking hard. "Yeah. Roger told me, 'Peter, my daughter, and grandson are watching you from heaven. You can honor and respect their memory forever, but you must find happiness for yourself, or they will never rest peacefully.' So, you're right, Judy, and that's what I will do."

"I'm glad," Judy smiled, her tears falling, but she was happy for him.

The following week was hectic with the funeral and how Mr. Rollins needed to find a new house. But Judy helped him with everything.

One day, he arrived at the office later than usual and gave her a to-go coffee cup. Judy took it gratefully and looked down at his shoes. They weren't dirty. He's really moving on.

A few days later, Judy was turning off her computer and getting ready to go home when he called her into the office. "Judy, would you like to have dinner with me?" he asked out of the blue. Judy could only nod eagerly, and they went to a great restaurant nearby.

From then on, he asked her to call him Peter and told her how much he had enjoyed her food. Judy laughed and told him about her family, growing up in a small town, her friends, and everything else under the sun.

His chuckles came often, and they made her heart skip a beat every time. She didn't know what the future would be like for them, but that was part of truly living.

What can we learn from this story?

• Don't let grief stop you from living your life to the fullest. Peter's in-laws wanted him to move on despite their terrible loss because life is short, and you can't waste a single day.
• Doing charity work and helping others is fine, but being kind to yourself is also alright. Peter gave everything he earned away, not caring about himself. But that's not right. It's okay to enjoy your money.

Share this story with your friends. It might brighten their day and inspire them.

If you enjoyed this story, you might like this one about a rich man who played with his maid's son while she worked, and later he asked the kid to lead his company.

This piece is inspired by stories from the everyday lives of our readers 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.