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How to Handle the Boss Trying to Date You

by Sherry L. Huckabee, studioD

While the rules against inter-office dating in general are easing, relationships with superiors are still heavily frowned upon. Such relationships are a natural target for gossip. Fellow employees will tend to suspect favoritism even where there is none, making you work harder for what you achieve in order to avoid the appearance of impropriety. When the relationship ends, it can be awkward for the entire office. If your boss makes an unwanted advance, it is important you handle the situation candidly and respectfully to avoid damaging or destroying your reputation or your career.

Be respectful. Your boss not only deserves your respect as your superior, but he or she can make things difficult for you, especially if hurt feelings are involved. Address your boss with direct eye contact. Do not put them down for asking you out or act upset about the request. Inform your boss simply and respectfully that you are not interested.

Deliver your "no" with grace and kindness. Rejection is hard for everyone. Remember how you feel when you are rejected and try to treat your boss with the kindness you would hope to be treated with. No matter how impersonal a rejection may be, it is hard for the other person not to take it personally. To soften the blow you can say something positive about your boss, express regret that you are not able to date him or her or let your boss know you are flattered, but you won't be able to oblige the request.

Respond quickly. Do not tell your boss you need time to think about it. In fact, it is probably better you don't take time to think about it or you might talk yourself into saying yes. Besides, you don't want to give your boss the idea there is a chance when there isn't.

Prepare in advance. The best way to guard against pursuit by the boss is to maintain a strict personal position against workplace dating. If your boss does ask, it is easy and truthful to say that you simply never partake in office romances.

Be honest. Do not say you are flattered if you are not. Do not say you don't date at work if you were out with the mail clerk last week. These things can help soften the blow if they are true, but a lie is never a kindness.

Don't gossip with others about the fact your boss asked you out. There is no need and it can potentially backfire on you.

Do not feel pressured. If your boss pushes for a yes, don't feel like you must offer additional reasons why you don't want to go out on a date. Being courteous or respectful does not require saying yes when you want to say no. You don't owe your boss anything. Besides, in a situation like this, the less said the better.


  • There is a thin line between natural attraction and sexual harassment. If you have respectfully declined, but your boss has continued to insist (or if he or she is making physical advances) then your boss is crossing the line into sexual harassment. In this case, you should consider reporting the matter to human resources or, in a smaller company, a trusted superior. Reporting is the best strategy. If, however, you don't feel you can report your boss, at a minimum keep extensive documentation so that, should it end up affecting your career, you have evidence regarding the inappropriate behavior.

About the Author

Sherry L. Huckabee graduated from the University of Miami School of Law. Although much of her career has been in the law, her BA in psychology has also served her well through raising birth, step and adopted children, and in endeavors including managing, teaching and traveling. She writes regularly on law, health, yoga, fitness, relationships, psychology and travel.

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