Quagmire of Office Dating



Should you date someone at the office? Maybe! We’ve seen some fabulous relationships develop…..AND we’ve seen it go horribly wrong and crumble into a hot mess. It depends on several things.

Screen Shot 2014-12-19 at 5.26.02 PMIf you are a bright, career-minded woman with a job you love at a solid company, your workplace may provide access to more like-minded single men than your extracurricular activities do. This difference is especially true if you’re working long hours and have limited social or church activities. Your workplace can offer a low-pressure setting to get to know someone, in contrast to the challenges of the “put yourself out there” dating scene of first dates, online dating, mixers, and fix-ups.

We KNOW dating is challenging enough! Throw office politics, gender differences, and business travel in there and there is your hot mess waiting to happen. So, yes. Your job may be a place to connect with others, but that doesn’t mean it’s always a good idea to date a colleague. In fact, there are some lines you need to be aware of and should NEVER cross.


1. Don’t date married men. It should go without saying, but affairs ruin promising careers and personal reputations. Just don’t do it. This kind of error in judgment is not easily forgotten AND those repercussions seem to be more serious and the transgression harder to forget if women do it. Why women are made to be the villains is not for today’s discussion, but we’ve seen women lose much so avoid this one at all costs.

2. Count the boss out. It’s just not a good idea to date your boss or anyone else who could be considered a supervisor. That situation easily creates an unhealthy power dynamic and can undermine your credibility with coworkers. You’ll be able to take full credit for what you achieve at work when there’s no question about influence or if anyone’s playing favorites. We’ve all heard those whispers of “she got there because……….”

Screen Shot 2014-12-19 at 5.25.06 PM3. Watch out for employee adoration. Remember that some may find your power and authority as a boss very attractive so watch out for those adoring fans whose interests may wane once you are not their boss or once you leave the firm. We have both seen office crushes go wrong, mostly due to office gossip and assumptions that people make. Remember, as a women in a big job, you are already in a fishbowl. People are watching and sometimes they don’t need much reason to try to tear you down. So be very careful of appearances.

4. Beware the fishbowl syndrome. Remember that a first innocent date can be twisted by those that might want your position so don’t give them any fodder. If you decide to date someone from the office, make sure you keep it private until things are serious and you have gone to HR and your boss first. We’ve seen someone’s fabulous VP job be ruined because she let a guy sit on a bean bag chair in her office after hours while she was working at her desk. Sounds innocent, and it was. But detractors only need you a tiny opportunity, so be careful and think about how things might look to others that don’t have your best interests at heart.

5. Check your company handbook. If your company has a formal policy against coworkers dating, honor it. You should honor the employee handbook, even if it means one of you has to find employment elsewhere. So should you jump ship on a great job just because a cute guy from the office winked at you in the elevator? No. But if you’ve gotten to know someone over time and you’re both serious about moving your relationship to a romantic level while your employer has a no-dating policy, then one of you should leave the company. If the romance works out, someone would have to transition anyway. If it doesn’t last, breaking the rules puts both of your jobs at risk. It’s best to deal with it proactively.


Screen Shot 2014-12-19 at 5.25.18 PMIf your company doesn’t rule out romance, and an eligible guy comes along, here are some guidelines we recommend that can make your journey smoother and protect your career:

1. Make it worth it. Sure, there are benefits to dating someone at work, but there are potential drawbacks too. In fact, working together can put unique pressures on a dating relationship. Those pressures COULD pay off in the end because you see your beau in various situations, understand more facets of his life, and have a clear picture of his financial security and career path. That familiarity is a fine line. While it would be great for knowing more about him sooner, it could also scare him away so use the information wisely, and file it away until things are more serious.

2. Keep in on the low down. Our friend Amanda met her husband at work. They handled work romance about as well as we’ve ever seen it done. She and her future husband didn’t work directly together, but they interacted enough that their relationship could have been disruptive to the office. They were careful and thoughtful. In fact, they played it so cool at work that most people didn’t even know they were dating until they were almost ready to announce their engagement! Your office romance doesn’t have to be top secret, but it shouldn’t be played out at work either. This approach is especially appropriate if you work closely with your beau.

3. Keep it civil. Sometimes relationships don’t work out. Remember, if the relationship doesn’t work out, you may end up running into your ex-boyfriend in the elevator, a meeting, or a performance review. Any of those scenarios are not nearly as fun as it may have felt while flirting with him as a potential boyfriend! You can’t exactly walk away from a guy if you break up and you may see him every day. You both need to recognize this possibility going in, have a plan, and strive to treat each other honorably no matter what happens. That stance includes maintaining discretion and confidentiality if colleagues ask about the break up…..and they WILL so be ready ahead of time.

Office romance can be a wonderful thing. Shared stories, common work friends, and the same industry means you have similar schedules and pressure points. AND it can mean wading in a quagmire of politics, gossip, and company policy. We hope these boundaries and guidelines we developed after decades of dating are helpful. Choose wisely, friend!