Pride logo

I Dated My Boss, It Didn't End Well

We thought we were being secretive but everyone knew

By Edward AndersonPublished 3 days ago 5 min read
I Dated My Boss, It Didn't End Well
Photo by Karthik Pillai on Unsplash

I first met Jeff when I walked into the engraving store in the mall. My initial thought was that he was super cute. Then I remembered that I needed to be asking for a job application, not interviewing guys to be my boyfriend.

My friend nudged me, she recognized that the cute guy made me forget why we were out at the mall in the first place. We needed new jobs.

"Excuse me, are you hiring?" I said.

"No," Pat said from the back. She walked out with a stern look on her face, I was convinced that she was the manager. Then she looked at Jeff, "are we?"

"No," he said. Then he looked over at me, "it doesn't hurt to take an application, though."

He gave both of us a paper application. I pulled a pen out of my pocket and filled it out fast. There was something about this man that made me want to be near him.

Once I handed it back to him, he assured me I would get a call for an interview. With a smile on my face, I left the store. Nothing could bring me down.

Nothing except the phone not ringing.

After three days of waiting, I called the store to see if I could figure out what was happening. Maybe he forgot about me. Or potentially he wasn't being serious when he said that I would be interviewed.

As it turned out, I did get the interview. And the job. And within a few days, Jeff and I were a couple. But we had to keep it secret.

---

Jeff was the company's regional manager, and he didn't want the other employees to feel like I was favored because I happened to share a bed with him. The boundary didn't bother me; I had long since learned that talking about my private life at work was a bad idea.

I quickly established myself as one of the best sales people in the district. Selling the engraving was easy for me, all I had to do was listen to what the customer wanted and then help them craft a message.

This helped ease Jeff's worry that I would coast along. He thought that it would take a while for me to catch up with Pat, who had been with the company for thirty years. He was impressed that I surpassed her sales in two months.

"I wish you could be the assistant manager at Macomb," he said.

"And what would happen to Pat?"

"She could retire," he said.

At the time, I thought he was being sweet. All he wanted to do was give me a boost up the ladder. He was looking out for his love.

Thankfully, the company was loyal to the employees that had been there for decades. Pat's position was safe from Jeff replacing her with me. But none of us were really safe.

---

As my sales exploded, more stores began asking for me to come work with them. Jeff had to approve me working at the other stores. And he would only do that if he were going to be at the store.

One of his favorite managers worked at the Lakeside Mall store. She requested that I come over and help her, she was short-staffed after a few associates quit unexpectedly. Jeff approved that right away.

I was to spend three days a week there and three days at the Macomb Mall store.

On my first day at the Lakeside store, Christian was assigned to help get me acclimated. The two of us hit it off and bonded over our shared love of Britney.

As guests came in, I taught him my methods to sell, and he taught me how to avoid the more difficult customers. It was nice to work with someone my age and that had a shared experience.

"Want to hang out this weekend?" Christian said as we locked up the store one night.

"That sounds fun. Call me and let's figure out what we're going to do," I said.

Jeff was not pleased when he heard that I was going to be hanging out with someone from work. I was confused by his rage but chalked it up to him being jealous that I was going to be with friends and not him.

"You know that he doesn't just want to hang out, right?" Jeff said.

"Christian has a boyfriend, I expect that he'll be joining us. You could too, if we didn't have to keep our relationship a secret."

Those are famous last words.

---

It turns out that secret kisses in the stockroom and your boss following you around Metro-Detroit are not ways to keep things a secret. People began to gossip about our relationship. Even Pat began to ask questions.

"Why do you leave with Jeff?" She said one night.

"It's my schedule," I said.

That wasn't good enough. The higher ups at the company got word that something was going on, and they launched an investigation into the situation.

Nobody ever asked me what was going on. But they got proof that Jeff was sleeping with an underling, and he was let go. I went into the Macomb store one day and learned from Pat that she had been promoted to interim store manager.

"Jeff was let go. No one knows why officially, but he called to tell me that it was because corporate found out about the two of you," she said.

"I didn't tell anyone."

That night I went home and called Jeff. As his partner, I wanted to offer him comfort. Maybe even help him find another job. Most of all, I wanted to tell him that I hadn't said anything.

But he didn't answer. In fact, I never spoke to him again. To this day, I don't know what happened to him or if he blamed me for his being fired.

For a long time, I took responsibility for what happened. I believed that I must have said or done something that led to him being fired. Even if it was unintentional, I still did something.

Those are no longer my feelings.

Looking at the situation through a more knowledgeable lens, Jeff abused his power. Dating someone under his employ was wrong. And using his position to ensure he had me under his control was an abuse of power.

I don't believe in regrets, they don't change anything. But this is one situation where I wish I could go back and advise my younger self to run.

Those are famous last words.

Relationships

About the Creator

Edward Anderson

Edward writes queer led stories that show that the LGBTQIA+ characters lives are multifaceted.

Reader insights

Be the first to share your insights about this piece.

How does it work?

Add your insights

Comments

There are no comments for this story

Be the first to respond and start the conversation.

Sign in to comment

    Find us on social media

    Miscellaneous links

    • Explore
    • Contact
    • Privacy Policy
    • Terms of Use
    • Support

    © 2026 Creatd, Inc. All Rights Reserved.