You can be on Entrepreneur’s cover!

I Dated My Coworker, We Broke Up, Then He Became My Boss. I Learned a Hard Lesson About Workplace Romances. Nearly 20% of respondents to a recent survey said being in a workplace romance negatively affected their career.

By Lara Sterling

Key Takeaways

  • Lara Sterling is a writer who had a relationship with a coworker.
  • After a devastating breakup, she found out her ex-boyfriend had been promoted to be her boss.
  • Looking back on her experience, Sterling doesn't recommend dating in the workplace.
entrepreneur daily
Gzorgz/Getty Images, D3sign/Getty Images, Abanti Chowdhury/BI via Business Insider
Lara Sterling (not pictured) dated a coworker in the '90s before they broke up and he became her boss.

This article originally appeared on Business Insider.

"I'm hoping we can put the past behind us and work together from here on without any problems," said my ex-boyfriend Austin (not his real name), peeking his head into my office.

I was reeling from the shock of talking to him for the first time after giving him the silent treatment for six months. But it wasn't out of nowhere; I knew why he was here.

Earlier in the day, I received a memo from the owner of the publishing company we both worked for announcing that Austin had been promoted to editor in chief of the magazine that I proofread and wrote for.

This meant my ex-boyfriend was now my boss.

Friendship turned into flirtation

Austin and I became friends a few months after I started working at the company. While we didn't work together directly, I interacted with him sometimes. During each encounter, he made me feel so comfortable.

He had big, kind eyes and a continual furrow between his eyebrows as if he was constantly stunned by the intensity of the world. But he wasn't shy; he was the type of person who never met a stranger. He had a nonjudgmental air to him, and even during our initial banter about office matters, I felt like we'd been friends for a very long time. He came off as incredibly intelligent, and I began to feel attracted to him.

This was the '90s, before many workplaces adopted strict "no interoffice dating" policies. But even back then, I knew that dating a coworker was a bad idea. "Don't get your honey where you get your money," the saying goes. What would the rest of the office think? Was I the type of woman who slept with the guys from the office?

Logic told me to suppress my feelings, but Eros is strong. I stupidly ignored my instincts and let myself fall for Austin.

One day, I was invited to lunch with a group of people from the office, and when I arrived at the café in question, I saw Austin was there. I took a seat beside him, and we chatted more. Before long, it was a given that we would eat together, flirting the whole time.

In many ways, he was the perfect match for me; we worked in the same industry and had similar aspirations. We were both driven to create and had similar tastes in cinema and books. We always had something we enjoyed talking about together.

One night, the sexual tension that had been building between us spilled over. We were both at the office late, and he came to my office to say hi. Taking a break from our respective projects, we sat together on the couch in my office. The energy between us was palpable. I fell into his arms, and he kissed me.

Keeping the office romance a secret

After that, we became an item.

Though our company didn't forbid colleagues from dating one another, we both already sensed the taboo nature of our dalliance, so we tried to keep it a secret. We pretended we didn't spend our nights together and made sure to arrive at work separately in the morning.

But then we'd spend lunch in his office, and I'd emerge afterward with ruffled clothes and messed-up hair. Obviously, we were doing more than just eating in his office, and the forbidden aspects of our relationship just made it more intoxicating.

I don't doubt that we were the source of a lot of office gossip, but at that point, I didn't care. I had fallen for Austin.

In retrospect, the smartest thing either of us could have done was to get jobs at different companies. But neither of us did, and this made things incredibly uncomfortable when we eventually broke up.

The relationship soured

It's hard to remember exactly how it happened, but as many couples do, we grew apart.

After a year of dating, we began to bicker, perhaps from being together so much. We worked together all day long, then spent evenings and weekends together. We never got a break from each other.

Hanging out all the time had engendered our connection, but it was also its undoing.

One night, we had an argument. I can't even recall what we were fighting about, but I assumed we'd make up afterward, as we always did. Nothing could prepare me for when Austin told me he wanted to end things. I begged him to reconsider, but he said it was over.

I was devastated. But more than that, I felt ashamed. It was embarrassing to get dumped and still be required to see the person every day.

In the past, when men have broken my heart, I've been able to lick my wounds in private. This time, I needed space, but I couldn't get it.

The following afternoon at work, I slammed my office door when I heard him talking to another employee nearby. I was hurt and out of control. If our coworkers had suspected we were dating, they definitely knew we weren't anymore.

It wasn't just that he had rejected me; our friendship was over, too. No more lunches together, no more joking around at the office. All I could do was avoid him to make things less painful for myself.

From that point on, I stopped speaking to him, icily looking the other way whenever we passed in the hall, and he, in turn, pretended I didn't exist.

I wouldn't be able to ignore him anymore

Things proceeded like this for about six months until I got that memo that Austin was now my boss, and it sent me into a tailspin. As my new boss, I would have no choice but to talk to him.

As Austin stood in my doorway after a year of ignoring each other, I wondered how I should respond. Could I put our past behind us now that he had become my superior?

It was easy for him because he was the one who had broken up with me. He wasn't the one with the bruised ego when our coworkers inevitably found out he had dumped me.

"No," I said.

Looking back, I can't believe I responded that way. After all, Austin had the power to fire me. Luckily, he didn't. He walked away, and I frantically searched my mind for another way to deal with this predicament.

I asked to be moved to a different magazine. The company we worked for published various magazines, so this wasn't an impossible ask. When I met with a senior executive, I didn't tell him why I wanted to move. A few days later, I had a new assignment, and Austin was no longer my boss.

I can't believe how unprofessional I was

I can't say I'd treated our breakup with much maturity. I was in my mid-20s and wasn't the most evolved human back then. I'm now 53, and I'm astounded by how unprofessional I was.

I know how easy it is to become blinded by one's emotions, and I completely understand why it's become commonplace for companies to have strict no-workplace-romance policies.

And yet, a 2023 survey by the Society for Human Resource Management found that 27% of respondents, all US workers, had been in a workplace romance. Forty percent said they'd flirted with a coworker, and younger millennial and Gen Z workers were 33% more likely to say they were open to interoffice dating than older generations.

I find these statistics shocking, knowing what I know now about how difficult it is to deal with a coworker you've developed feelings for if it doesn't work out.

The same survey found that nearly 20% of respondents who'd been in a workplace romance said it negatively affected their career. When you add in the chance of sexual harassment allegations, I would never recommend dating a coworker. Even if you work in different departments, dating a coworker is opening a Pandora's box of emotions that are difficult to navigate professionally.

I quit the company about a year after Austin got his promotion, and I haven't had another workplace romance since. Though the experience didn't impact my career negatively, it did affect how people saw me at that company. I lost the respect of my peers, and that's a sensation I never want to feel again. I learned my lesson.

Lara Sterling is a writer living in Los Angeles with her husband and two children.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Resumes & Interviewing

Build a Better Resume with This $35 Subscription

AI Resume Builder promises to help you apply to jobs twice as fast.

Side Hustle

He Took His Side Hustle Full-Time After Being Laid Off From Meta in 2023 — Now He Earns About $200,000 a Year: 'Sweet, Sweet Irony'

When Scott Goodfriend moved from Los Angeles to New York City, he became "obsessed" with the city's culinary offerings — and saw a business opportunity.

Marketing

I Got Over 225,000 Views in Just 3 Months With Short-Form Video — Here's Why It's the New Era of Marketing

Thanks to our new short-form video content strategy, we've amassed over 225,000 video views in just three months. Learn how to increase brand awareness through short-form video content.

Business News

Samsung Makes 6 Day Workweeks Mandatory for Executives as the Company Enters 'Emergency Mode'

Samsung said its performance "fell short of expectations" last year. Now executives are required to work weekends.

Productivity

6 Habits That Help Successful People Maximize Their Time

There aren't enough hours in the day, but these tips will make them feel slightly more productive.

Leadership

You Won't Have a Strong Leadership Presence Until You Master These 5 Attributes

If you are a poor leader internally, you will be a poor leader externally.