A workplace romance can be really fun. Many people find their spouses from work, and it makes sense since you spend so much time with your coworkers. Dating your boss, however, is a totally different kind of fish. Here’s how to date your boss. 

First thing’s first. Have you considered the pros and cons of dating your boss? There are good and bad things about dating someone at work, but the number of cons definitely increases if your partner is also your boss.

For one thing, some places forbid it in the contract/company policy. It can be an HR nightmare. So before you get into things seriously, find out if you’re even allowed to.

Pros vs Cons

The pros to dating your boss should be the same as dating anyone else. At no point should you think you’ll get benefits at work because of your relationship. You might get benefits, but if anything, these could work against you.

There’s definitely something inherently sexy about the idea of dating your boss. Especially if they’re really good looking. Office fantasies, light work flirting. It can be a lot of fun! A good pro is that you’ll be able to spend a lot of time together since you work in the same place.

Cons to look for include office gossip. If you date your boss, word will get around. Even if you go slow or keep it secret at first. You have to remember a lot of people may take it negatively.  Some may even be jealous.

Long-term consequences also need to be looked at. If things don’t work out, how will that affect your career or references for future? If you’re serious about the relationship then it’s good, but consider the risks if you were thinking of something simply casual.


Besides break-up problems, there may be other consequences you need to look into. How would you feel about getting a different job, or changing departments if the need arises? Are you ready to take on those sort of responsibilities and risks?

If you’re dating your boss, you also need to set ground rules within the relationship. Your work relationship and your personal relationship might have different dynamics. It’s important to be clear on expectations and how you’ll be treating each other. You’ll need to know how to stand up against your boss on personal affairs, as in relationships both partners should be equal.