Roommate Workplace Short Stories & Novels

My supervisor, Jessica Lawson, spotted me coming and going from a multimillion-dollar oceanfront estate in the Hamptons. She decided I'd landed a wealthy man and was about to marry into money. That same night, she dropped the estate's location into the company group chat and invited everyone to a department party there. "Emma Bennett is hosting at her oceanfront estate this weekend. Bring your families. Everyone in the department is invited!" I patiently explained that I was just a part-time caretaker. "My job is literally walking the owner's dog." But the group chat went feral. Everyone ignored me and started placing orders. "Remember to open the Romanée-Conti early so it has time to breathe." "Pick me up in the Lamborghini that day. Ferraris just aren't my vibe." In under ten minutes, more than fifty people had signed up. Jessica tagged me directly. "The catering bill is going under your name. Make us proud, and don't embarrass the boss." I gave a humorless laugh at the endless sign-up list. Richard Hale, the estate's owner, was a boxer who stood nearly six foot six and was built like The Rock. The last thief who trespassed on his property is still in a coma.

My girlfriend, Olivia, had one way of measuring how much I loved her: how fast I replied. In the two years we dated, she blocked me 88 times. The first time, I was in the shower and missed her call. The 17th time, I was bringing her coffee when I missed a message asking for extra ice. The 56th time, I was at dinner with a client and didn't respond quickly enough to a video she'd sent me. This time, I worked until ten and missed the 9:50 p.m. movie she'd asked me to see with her. I told her there was a problem with the project and my manager wouldn't let me leave. She just laughed. "Anyone who really loves me would make it to a movie even with ten minutes' notice." When I got home that night, she'd changed the door code and removed my fingerprint from the lock. I sat outside all night. After work the next day, I went to her favorite jeweler and bought the necklace she'd wanted for the past three months. I kept telling myself I hadn't done enough. I just needed to do a better job balancing work and our relationship. She was in the shower when I got home. Her phone lit up on the dining table. A notification from a group chat called "Do Not Bring Him Tonight" flashed across the screen. Olivia, her childhood friend Ethan, and my best friend Daniel were all in it. Daniel had sent a voice message. "Olivia, I'll keep Chris at work late again tomorrow. Let's see if he chooses overtime or you." Ethan replied almost immediately with a laugh. "I found another beautiful piece of jewelry. It costs three times his salary. Send it to him and see if he chooses his paycheck or you." That was when I finally understood. I hadn't failed to prove that I loved her. They'd been setting me up to fail from the beginning. And if that was how things really were, I was done.

Being a good saleswoman means knowing how to make money and save it. So when my landlord said someone wanted to split the rent with me, I jumped at the chance. My new roommate kept regular hours. He was neat and even knew how to cook. His only downside was that he barely talked. But to me, that was a plus. Quiet and emotionally stable. Perfect. Then came the year-end company meeting. As the top salesperson, I was invited to sit with the executives. The man at the head of the table looked up. His expression was cold and distant. My manager introduced him as the heir to Prescott Group. Except... I could've sworn he was my quiet roommate. I'm speechless. Here's the thing. I got drunk last night and accidentally ripped his pants and boxers. Think I still have time to sew them back?