Doc Love Advice: The Pros & Cons of Dating at Work

I’m going to start in a positive way. Dating at work has some pros, despite the challenges it also poses, and it could be the right decision if you meet the right person – in the right circumstance.

Let’s go over the pros and cons of dating at work so you know what you’re getting into before you ask a colleague on a date.

Coworkers develop a sense of familiarity with one another – even if they don’t work in the same department. You work for the same company so you have a lot to talk about and can share in a common cause. It should be easier to develop a rapport with a colleague. Sure beats meeting a complete stranger from an online dating app!

As much as I love — and recommend — online dating, I won’t pretend that it’s perfect. Online dating can feel artificial at times. Daters experience a built-in pressure to turn a stranger situation into a relationship situation – because what are you there for otherwise, right?  

If you are on an online dating site, you are likely trying to meet Ms. Right, and she’s likely trying to meet Mr. Right. It almost feels as if the clock starts ticking with that first message. How long will it take for you two to stop chatting and go on a date!

On the other hand, when you casually get to know someone in a work situation the relationship can sneak up on you in a good way.

A work environment offers daily insight into a person’s character and sense of humor. You’ll generally see the real person as you get to know each other over time at work. You’ll learn how she handles stressful situations and communicates with her coworkers or colleagues. You’ll know her reputation and her work ethic. 

You can get a much clearer picture of another person while at work than you can in other settings. Say met someone at a bar and you are on date five when Ms. Sweet Personality all of a sudden loses her temper at a car that cut you off. You see the veins on her neck pop as loud as the volume of her scream, and you’re thinking “Whoa, who is this person?”  

Bottom line, a single person will probably encounter way fewer surprises with a coworker than with a stranger off the street or the online scene. Even if you don’t work in the same department, you can get to know the person at least a little bit through her work achievements and her colleagues before asking her on a first date. 

So far, dating at work sounds like all rainbows and sunshine, right? Well, some nice upsides come steep downsides, so here are three cons of forming a romantic relationship with a colleague..

After two coworkers break up, they still have to work together. The heartbroken couple will likely continue to see one another every day, maybe all the time if it’s a small office. 

If you’re dating a woman you met at a wedding, you can break up and never run into each other once. If you started a long-distance relationship online, you have nothing to stop you from ghosting and moving on without awkward encounters with an ex.

When a random woman blows you off and ends your dating relationship, she can fade from your memory because you never saw her before you dated her, and you will likely never see her again. No big loss!

But a woman you’re dating from work?  If she dumps you – or you dump her – you still get to see her every time you go to work. Bottom line?  The potential for very uncomfortable gossip, silent elevator rides, and stilted lunchroom encounters is a big con to dating someone at work. And the smaller the company, the bigger the risk of it getting way awkward!

What are the rules of personal relationships? What if she turns out to be vindictive or unbalanced? You might think you know her, but as I coach in my SYSTEM/DATING DICTIONARY, you don’t really know a person until you have been seriously dating for a couple years. And even then you should still be watching.  

She can present an amazing image for awhile, and then you find out it was totally false. If she’s a coworker, she may cause enough trouble or spread enough rumors that HR gets involved. If she accuses you of sexual harassment, you could face serious consequences in your career.

You need to tread carefully in relationships with colleagues. You don’t know what could happen after a breakup, and the situation could escalate into a problem for the company as well.

Listen, I’m not saying it will happen but if you think it can’t happen then perhaps you haven’t been paying enough attention. In the real world, you are absolutely risking your job the moment you start a romantic relationship with a coworker.

A lot of people have their work personas and their personal personas. And they like to keep them separate.

Personally, when I worked in corporate America I would have rather had a root canal than  let any of my peers, subordinates or superiors know deeply personal stuff about me.  

Well, if things don’t work out with your love interest slash work colleague, your personal life is going to collide with your work life. All the personal information you shared with her suddenly becomes fair game for office talk! 

I can almost hear you countering, “She’d never do that Doc! She’s not that type of person!’ 

Oh yeah? Scroll through the social media feeds of recently broken up couples. I bet many of them started with sweet nothings and romantic ideals. They too would probably have said they’d never ever talk bad about you to other people. Until you made them angry. Then all bets are off!

As a men’s dating expert, I advise singles against dating someone they know at work. The upside can be nice, but you need to think of your paycheck and career ahead of any short-term romantic interests.

The downsides outweigh the upsides in this circumstance. You can find plenty of ladies out there without this type of risk profile. 

As I always tell my students, I am an odds maker at heart. When I tell you the odds are against your relationship with a coworker, I’m not telling you absolutely don’t do it. I just want you to realize the reality of the situation.

Remember: Dating at work can carry a lot of risk. Think carefully about the pros and cons before you take that step with a colleague.