When you are romantically attracted to your female boss, the prospect of asking her on a date is fraught with potential problems--for you and for her. If the attraction is casual or purely physical, you would probably be wise not to ask her out. However, if your romantic passion is so powerful that you simply have to take a shot, you can ask her in a way that is most likely to protect you both from embarrassing or career-threatening conflicts.
Review your employer's policies. No laws prevent employees who share a work environment from dating, but psychologist Gary Vikesland notes on the Employer-Employee.com website that laws also don't prevent employers from prohibiting the practice within their organizations.
Discuss your intentions with a discreet person in your workplace. If you feel comfortable talking about it with a superior whose rank is equal to or higher than your boss, doing so may be helpful for several reasons. The superior may give you insight into the particular problems that dating a subordinate could pose for your boss. The fact that you made your intentions known to a superior beforehand could work in your favor if anyone makes false accusations about your behavior or claims you violated company policy.
The superior may also have ideas about how your boss could delegate her authority over you to another party if she is interested in dating you but does not want to create a conflict of interest with her work duties. Finally, the superior might be able to talk you out of it, which could be for the best.
Choose an appropriate location to ask for the date. You will want some privacy, but the moment shouldn't be too private. Sexual harassment laws don't just apply to bosses who exploit subordinates. Even though you're not the one in power, someone could still accuse you of what the law defines as "unreasonably interfering with an individual's work performance or creating an intimidating, hostile or offensive working environment."
If you're alone with her in an office, make sure the door is open. Consider asking her out in a common area, such as a break room or cafeteria, where other people will be nearby and will able to see, if not hear, your conversation.
Ask your female boss to share a casual after-work activity, preferably one you both enjoy. If you share an interest in a particular kind of music, food, art or sport, the date should involve that interest. Vikesland recommends that workplace romances should progress as slowly and as casually as possible. Picking a dating activity that could also be construed as a friendship activity will help keep things casual and relaxed in the beginning.
When asking her out, acknowledge the potential conflicts. Let her know you're aware that women often struggle to be taken seriously as leaders in the workplace and that dating a subordinate could undermine people's perception of her. She, of course, will probably be all too aware of this hazard, but she may find it reassuring that you understand and are open to exploring ways of minimizing the problem.
Emphasize that you are interested in her as a person, not in what she may be able to do for your career.
Back off immediately if she says no. Even if she turns you down in a vague or open-ended way, suggesting she might be interested in the future, do not ask her out a second time if she says no the first time. Do not interpret vagueness as an invitation to keep trying; assume she is sparing your feelings. Consider the matter closed unless she brings it up again and clearly expresses interest.
Scott Roberts studied communications at the University of Southern Indiana and has written for local newspapers throughout his adult life. He has created articles for more than 70 international clients. An accomplished artist, he has illustrated and written cartoons for newspapers and GoComics.com. He lives in Southwest Michigan.