The funny thing about single life post-college is that, for most of us, we don’t interact with many different people during the workweek. We see the same faces over and over again. If one of them happens to be appealing to us, it is only natural to feel a desire to pursue it. The romantic in all of us likes to believe that “love conquers all,” to hell with the consequences. Dating your boss is risky, but many people take the leap of faith.
The Consequences of Dating Your Boss
Statistics show us that roughly half of all married couples met at work. On the other hand, there is no study showing how many relationships at work failed. Unlike a typical breakup, the wounds of breaking up with someone from work are constantly poked and re-opened from the close proximity of the person. For that reason alone, it is wise to be extra careful before flinging your emotions or your panties at the hot guy in the cubicle next to you or your boss. Dating your boss or a co-worker can be tempting, but be careful. Of course, if you feel very strongly that he could be the one, who am I to tell you it’s wrong?
Taking Chances By Dating Your Boss
Both life and love require us to take some chances and dating your boss is one. If you plan on staying at your job and feel that dating your boss would not make things complicated then go for it. Unfortunately dating your boss can be difficult because it might not work out. Would you be able to keep your job, if you break up? Will you be able to maintain a friendly relationship with your boss if the romantic relationship falls apart? Dating your boss can be very tempting, but you have to consider the possibility that it might not work out.
If you are leaving your job and interested in dating your boss, then just take a leap of faith. Why would you NOT go for it? Just make sure that if it does not work out, it will not affect your future job opportunities or reputation. Discretion is always advised with dating your boss or a co-worker. Work relationships can create sticky situations when things go sour, but since you already have an out, I say go for it girl!
The Pros of Dating Your Boss:
1. You know he or she has a job and is responsible.
2. One big major benefit of dating your boss is that you already know what things you have in common.
3. Makes having a quickie a little easier. Perhaps you guys can get it on during your lunch break.
The Cons of Dating Your Boss
1. Dating your boss can sound exciting. Sometimes relationships that are usually seen as taboo can be a major turn on. Unfortunately, dating your boss can be dangerous. If it doesn’t work out there is always the possibility you might also lose your job.
2. If you guys get into an argument, it might make your work environment uncomfortable. It will be difficult for you to take some space from each other.
3. Just because you’re dating your boss doesn’t always mean you will get away with whatever you want. If you want to call in sick, but you aren’t sick your boss will know the truth and may not like it.
Tips on Dating Your Boss:
1. When dating your boss, don’t mix business with pleasure (except for the lunch time quickies of course, you are off the clock). Keep your arguments out of the office.
2. Make sure your boss is single. Dating your boss married boss is a recipe for disaster.
3. Dating your boss may seem like no big deal to you, but your co-workers may view it differently. Try and keep your relationship private.




You should never date your boss. That is gross. Well I guess if you stop working for your boss than it is ok, otherwise it is simply gross. Unless he is hot hahahaha.