12 Do’s & Don’ts I Learned From Dating A Coworker

By | Saturday, December 12, 2020

I’ll admit — I’ve dated a coworker before.

If your eyebrows are raised, good. That’s the correct response. But it’s true; my longest relationship was with a former coworker. We dated for four years, and we managed to outlast our involvement at the company, but ultimately it was one big, longwinded learning experience.

So, I want to preface this article by saying I don’t recommend dating coworkers. I don’t regret the experience myself, and it can work (my parents met through their work), but it is a frustrating and largely unfulfilling balancing act. You need a lot of rules in place in order to not damage yourselves, your company, your coworkers…It’s not worth it unless you’re absolutely sure that person is “the one,” and in my case, well, it wasn’t.

Once more — I don’t recommend doing this. That said, here are the do’s and don’ts I picked up along the way:

1. Do: Seriously consider whether it’s worth it.

As I mentioned, my parents met at work. They’re still going strong after almost 30 years! That’s great, but don’t expect it to be the norm. Think very seriously about whether you’d be comfortable in your job if/when things don’t work out. Is this person really worth giving up this aspect of your career, should things fly south? Think hard.

2. Don’t: Rush into it.

When my ex and I started dating, it was a very strange circumstance. Not only were we working at the same startup, but our CEO was the one who pushed us together. Seriously. For what it’s worth, I will say that this was a true startup environment, and the CEO and I had been friends before working together. Still, it’s a strange feeling to have your boss push you to date someone, let alone a coworker.

I remember my first day on the job, the CEO asked me to join her for dinner. I obliged, and during that dinner — in front of another coworker, no less — she suggested that my now-ex might be a good match for me, romantically, and went so far as to ask whether I thought he was attractive. A month or so later, he asked me on a date, and after some back and forth, I agreed. There was no reason to bite the bullet so quickly. We didn’t wait that long, but it probably would have done both of us some good to get to know each other better as friends before going on that first date.

3. Do: Establish ground rules early and often.

On that first date, we talked about a few things:

  1. How this was a very bad idea — dating a coworker secretly in a startup could only end poorly.
  2. If this date was the only one we had, we would not interact differently at work.
  3. If this date was not the only one we had, we would not interact differently at work.
  4. Our mixed reviews of the recent Star Trek movies — hey, it was 2013.

Obviously, it wasn’t the only date we went on. After that, we decided that we would not be alone together in the office, and we would not have any displays of affection around coworkers. Period. Rules changed and evolved over time to include:

  1. No talking about our relationship at work.
  2. No working on projects together.*
  3. Not having any sort of managerial relationship at work.
  4. We would absolutely not work within the same department, in any capacity.*
  5. We would not arrive nor leave together (although when we moved in together later down the line, this rule was abolished).
  6. No displays of affection when around coworkers, regardless of context or circumstance.

Some of these were good, smart rules. However, some (*) were just plain stupid or unrealistic. How, in a startup of 15 people, can you avoid working on projects together? But for non-startup situations, you can probably find a way.

4. Don’t: Let the relationship and your job take over your life.

We were in an eat-sleep-and-breathe startup. Work-life balance did not exist. In fact, we were literally living with our co-workers for a year before we moved out of the company house and into our own apartment. That rule against any public affection meant that, even when we were at home, we were distant and even borderline cold to each other. We were so diligent about not being seen together that we, well, didn’t actually see each other.

Fortunately, this got better when we moved out of the company house. Unfortunately, each of our closest friends was involved with the startup, so outside social events were few and far between for us. This may have turned both of us into hermits as the years went on, and he stayed uncomfortable around my friends long after we left the company. Still, we were working around the clock most of the time, and along the way at least one of us lost touch with the hobbies and people that really mattered. It wasn’t a healthy way to live — if life is entirely devoted to work, even in your relationship, you’re not really living.

5. Do: Be considerate of your coworkers.

You’re going to get closer with this person than anyone should be in an office environment. All of the interactions that generate or stem from attraction are inappropriate for the workplace, so keep that shit under wraps. I’m not just talking about physical affection like holding hands or kissing, or what have you. This can be personal discussions, banter, inside jokes…Things that wouldn’t be a part of your 9-to-5 in any other circumstance. Nobody wants to be the third wheel in a boardroom. Consider your coworkers’ perspective, and don’t wallow in your romance. Get work done, and keep the relationship out of the office, where it belongs.

6. Don’t: Expect it to stay secret forever.

I’m not saying one of you will start the rumor, but despite even your best efforts, someone in your office is bound to notice at some point. One ho-hum date might slip under the radar, but if you’re involved with each other beyond that, get ahead of the rumor. Talk to your supervisors and/or HR before they catch wind of it from someone else.

7. Do: Confirm whether there’s a company policy about dating in the workplace with your HR department.

No matter your intentions at the beginning of the relationship, things can (and likely will) go wrong at some point. Lucky for us, things didn’t fizzle out until a year or so after we left the company. That’s not the case for most of the coworker relationships I’ve seen, though! So check your Employee Handbook and talk to HR. They’re not going to fire you for asking a question. In all likelihood, there will be a policy in place — usually saying that you each need to disclose the relationship to HR and sign a paper saying it’s consensual for both parties. It’ll also likely state that neither of you can directly or indirectly manage the other. Respect whatever rules the company has in place, and ask for direction or help if you need clarification along the way.

8. Don’t: Date someone whose career you have any control over, and vice versa.

Even if the policy doesn’t restrict dating at work between managers and subordinates, you don’t want to go there. In the best circumstance, you’re both good employees doing well and you’re seen as picking favorites — alienating each of you from the rest of the department. In the worst circumstance, someone underperforms and it affects the relationship. Luckily this wasn’t my situation, but seriously. I’ve seen it happen. It’s not worth the effort.

9. Do: Talk about work.

We had a lot of late nights and weekends in which we’d work nonstop. We talked about the frustrations of being in a 24/7 startup, or how we felt about new hires. There are emotional benefits of sharing the challenges, wins, and concerns with someone who knows first-hand what’s going on with the business, as well as practical benefits of being able to problem-solve together. Talking about the work we were doing brought us closer because we were both sharing a big burden, and each had a different perspective on it. In a lot of cases, we were able to brainstorm and attack work-related problems together at home and come back to the office with a game plan. That said…

10. Don’t: Only talk about work.

For a few weeks at a time, work would consume us. We’d have our laptops out and only talk to each other to ask for feedback on the presentation, or suggestions on a design. Working together (out of the office) was fun, but we desperately needed something else in our shared lives in order to keep growing together.

11. Do: Kick ass at your job.

Don’t give anyone a reason to think you or your partner are negatively affecting each other’s work. Stay focused and on top of your projects. I’m not saying just proceed, business as usual. I’m saying overcompensate because people’s impressions of you will change as the cat gets out of the bag. Perception is often more powerful than the truth, so don’t give them the chance to think you or your partner are slipping.

12. Don’t: Keep the relationship going just because you work together.

This has been a revelation for me, looking back. Whenever a red flag came up, I would tell myself to make it work — and I’m sure he did the same. Clear incompatibilities were smoothed over because it would be harder to work together as a failed couple than it would as a less-than-happy one. I’m not saying there weren’t highs and lows throughout our relationship, but things like clear incompatibilities on whether we wanted kids, his dislike of my cat, and whether I’d take his last name down the line were all blows to our relationship — and things we would never yield on. We knew about these things for years and still stuck it out, only to argue about them down the line.

If we weren’t tethered to each other by the company, we probably would have saved ourselves a lot of time and heartache.


Good talk? Good talk. To recap: do as I say, not as I do. But, if you have to go fishing in the company pool, at least wear a life vest. Keep tabs on each of your needs, and don’t let merging romance and work take over your life completely.

Tis is a 20-something recruiter, startup enthusiast, finance blogger, and proud feminist-slash-crazy cat lady. Find her on Twitter or check out the blog for lifehacks and musings on personal finance, professional growth, and enjoying the journey to early retirement.

(This article was originally published on February 21, 2018)

Image via Unsplash

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