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Dating a superior at work can often end badly

DEAR J.T. & DALE: First, I’m Latin, and my culture is absolutely Latin. I started a new job six months ago, and in the past two months I’ve been seeing my boss with different eyes. I’m almost positive he’s feeling something, too. (He’s not my direct boss; he’s about three levels over me.) We talk and make jokes, and he moved his office near mine. I know our cultures are different, so I don’t want to be aggressive. Could you please let me know what Americans think about this situation? – Emma

J.T.: You are wise to ask. Dating at the office is not considered a good idea. While it is not illegal, it is generally frowned upon. There are several reasons that dating a superior is a bad idea. First, the company may have a policy against it. If that’s the case, and you two start to date and get caught, you both will be fired. If there isn’t a policy and you start dating and things go badly, he could decide to have you fired. Or, if you no longer want to pursue the relationship and he does, you may find yourself in a situation of sexual harassment. This could lead to your filing a lawsuit, which is messy and likely would hurt both your careers. Finally, if you are flirting too much, having misread his pleasant behavior for more than it is, he may report you to the HR department and you could get in trouble for sexual harassment. In short, in America, there is just too much that can go wrong that makes dating in the office not worth it.

Dale: It’s a sad commentary on modern life that it falls to me to be the romantic on the team. Sure, it’s a terrible idea – which, come to think of it, is exactly what everyone told Romeo and Juliet. And how did that turn out? Ouch. Here’s the point: There’s no way to stop people from falling in love. In fact, some people find the danger tantalizing. So, what do you do? J.T. is right about not being aggressive: Do not force the situation. On the other hand, having a friend/ally three levels above you could be very helpful. So why don’t you ask him to be your mentor? If he agrees, you can be open about spending extra time together. It also puts the relationship in clear business terms. Try to keep it that way … but love happens. Just don’t forget how it worked out for Juliet.


Dear J.T. & Dale: I just got an offer from a company, but last week I interviewed for my dream job. Is it OK to tell the first company that I can’t accept the offer until I hear from the other firm? – Kendall

J.T.: No, it’s not OK, and it’s the fastest way to have the offer rescinded. Just like in dating, no employer wants to hear that it is the backup when the first choice isn’t available. I would contact the dream employer and say: “I’ve just received a job offer, but you are my first pick. Can you tell me if I’m still in the running for your position?And if so, what the rest of the process is like, as I need to decide if I should turn down this other offer, given that I really want to work for you?” If you share this information, the employer will be honest with you about your candidacy.

Dale: Yes! Having another offer is catnip to an employer. I’ve seen it happen again and again: You get another offer, and suddenly you’re the hot prospect and they can’t hire you fast enough.

J.T.: However, if that doesn’t happen, and they still don’t have a decision for you, I would go ahead and accept the job with the other firm. Most likely, you won’t start for a couple of weeks. If, in that time, you get the other offer, you can always call them and let them know. You likely will burn a bridge, but sometimes that is what happens in job searches.

Jeanine “J.T.” Tanner O’Donnell is a professional development specialist and the founder of the consulting firm jtodonnell. Dale Dauten resolves employment and other business disputes as a mediator with Please visit them at, where you can send questions via email, or write to them in care of King Features Syndicate, 300 W. 57th St., 15th Floor, New York, NY 10019.