Should I Date Someone Who . . .

Should I Date Someone Who Works With Me?

It’s important to keep in mind that your specific case may have more practical considerations than the Two Chis. My first questions would be, “How much do you care about your job?” and “How large is your company?” If you care a lot about your job, then you should be really reluctant to consider dating in the workplace. If the relationship goes under, then you’ll be losing both a partner and a potentially rewarding career. If the company is larger though, then there may be more opportunities to move around should the worst happen. Having said that, dating within the workplace is extremely alluring and one of the most frequent places where people nowadays say they met their significant other, so you should never say never.

Character: If the person you’re dating is your superior, then that should raise a flag. It’s not an automatic deal-breaker, but you have to see how this reflects on their character. Do they have a prior history of picking up subordinates from the office? If yes, then your potential partner doesn’t seem to have a strict enough moral compass to keep themselves in check. There is a spoken and an unspoken rule about superiors dating their subordinates, and so your superior should only pursue something with you if this time is really an exceptional case. Even if they do decide to proceed, they should at least appear to be cautious and show reservations.

If they’re flagrant about it, and have dated subordinates before, then they probably lose points on the fairness aspect of character. Superiors have an automatic power advantage, which is very easy to abuse. If they seem casual with using that power, then you may have trouble getting what you want or finding compromise later down the road.

If the person you’re dating is a subordinate, then that should raise a flag as well. Again, dating within the workplace is like the Rubicon, it should only be crossed in exceptional circumstances. Does your partner have a prior history in the workplace? Are they very carefree about it, throwing caution into the wind? If so, then this person is someone who is potentially very irresponsible and/or uncaring. This is someone who doesn’t care what other people think of them, and so how can you be sure they’ll care what you think about them?

Chemistry: Dating within the workplace is usually extremely appealing. So, I would be curious to see what your interaction is like outside of the workplace setting. If you go on a trip together (for something non-work related), are all the sparks still there?