Tips for Dating Your Boss

Tips for Dating Your Boss

Dating your boss can be exciting, but there are some tips to keep in mind if you do not want your love life to interfere with your work life.

People fall in love all the time. At times, this occurs at work as you interact with the same person day in and day out. Sometimes, it is even with your boss. Since you are together all day, have similar fields of work and know you can communicate, it can be easier to handle passions and interests because they are aligned. While this may seem ideal, there are things to consider.

Dating a Boss

There are some good things to dating a boss or anyone from the workplace. The pros and cons are numerous. A pro, or a con depending on your preference, is that you et to spend a great deal of time together, both at work and on a date.

First, consider that if you are simply falling for your boss, and not already dating, that it will complicate work overall unless very clear boundaries are put into place. If you are already dating, then put  few things in place to keep things on the right track whether the relationship works out or not.

Are you really in love?

At work, falling for a charming boss is an easy task. This is likely someone you admire as they offer inspiration. You may wish to spend time with them as a way to fulfill a subconscious need for acknowledgment and attention. Having these feelings may not be love, simply a longing. This can be hard to differentiate if your boss is flirty or occasionally sneaks a peak at you.

This is natural and there is no need to feel bad. It could be just you trying to win their praise in any way possible. In pursuit of this praise, you may inadvertently flirt or fall in love (or lust) when the goal was to be impressive.

Is dating a boss a good idea?

Though office romances are common, both physically and emotionally, they tend to be looked upon poorly. While dating a coworker is one thing, a boss is not truly a safe bet. Regardless of your intentions, people will assume you are flirting to move ahead in your career. If you go forward anyway, it should be discussed up front whether the relationship is to remain secret or be led in the open. This can have a big impact on both your lives.

Secret Relationships

Secret relationships are exciting and often fiery, but being in a relationship that has to be kept secret can easily lead to feeling insecure. You will always question if you are the first or the only relationship that is being kept secret. It could be your boss is simply enjoying the ability and willingness to keep things secretive.

There have been times when a boss purposely flirted to get a workers attention and to cause them to fall for him or her. This is just a way of playing people to their advantage. If you do pursue a secret relationship and are certain you are the only one then that is wonderful, but if you feel like there could be others, beware. You could end up devasted, confused, and unable to discuss the problem with anyone.

What to Consider when Dating Your Boss

There is always a chance of a perfect relationship resulting from dating your boss, but it is always best to be safe.

Draw the Line

Never allow your personal and professional lives to mix. At work, you are paid to work, date on your own time.

Stand Up for Yourself

Remember that your boss is only your boss at work. Stand up for what you want and need in the dating aspect of you may end up being taken advantage of over time. You may be a subordinate at work, but in the separate personal relationship, you are equals and it must stay that way.


Public displays of affection can be sweet and can be hard to avoid, but if dating your boss, avoid this when in the public view. Being overly flirty in the office or showing signs of dating can give reason to coworkers to dislike you.

Potential Downfall

When you are dating a boss, you are in a vulnerable position. You have to trust in your boss’s ability to keep personal and work life separate if a problem arises or you break up. If they are angry you could suffer at work or if you separate, you could end up unemployed. This is a tricky position.

Peer Concerns

If the relationship becomes public or the gossip mill starts working overtime, your peers may start to think less of you. Any successes you have at the office will be attributed to the relationship, no matter what. If you mess up, they will always feel you were let off easily. This can lead to a hostile environment.


Though you may try to keep the relationship separate from work, repeating office gossip or comments when away from work can be a problem. You may not intend to share, but this insider information can affect the decisions made by the boss. It can be a problem if you do share, but awkward if you don’t.


All offices have gossip, especially when there is little else going on. Once the rumor you are dating the boss gets started, you will no longer be known for your work, but for your personal life. Every time you are alone with your boss, even if it is innocent, the gossip mills will grind again.


If your boss, or you, have to spend lots of time with someone else at work, jealousy could develop. This is with or without flirting. You may start trying to control each other’s work time which can be a problem.

Secret or Open

Some offices have a clause about revealing office romance as part of the contract. A few prohibit it completely. Even if there are no written rules about this type of contact, you both need to be clear about how it will be handed with others in the office. Coworkers who know could be jealous or petty, but not sharing could be a free pass for your boss to behave however they desire. Set clear boundaries.


Assuming you are keeping the relationship secret, you must be prepared to handle work interactions when another coworker shows interest in the boss. A project or meetings could bond them and you must maintain your cool or move on.

Relationship Endings

We cannot predict the future. While your relationship can be perfect at the moment, it may at some point end. If the secret is shared or you break up, this must be properly handled. If you think the risk is worth it, then date but start looking for other employment. If you do this, then even if the news is known, the gossip will not be an issue. This also means if the relationship ends, your future is secure in a new position.

Choosing to date your boss is a personal decision. It can be fun and exciting, but you must make sure your mentally prepared for both the best and the worst. Always protect yourself personally and professionally.