I work with a woman that I am interested in dating. We are almost the same age and have an excellent working relationship. She has dropped hints that appear to indicate she's also interested in me. I have a close friend who lost his job because of workplace sexual harassment, so I know I have to be careful. How can I ask her out without risking my job?

Dear Molly,

I work with a woman that I am interested in dating. We are almost the same age and have an excellent working relationship. She has dropped hints that appear to indicate she's also interested in me. I have a close friend who lost his job because of workplace sexual harassment, so I know I have to be careful. How can I ask her out without risking my job?

-Dave

Good question, Dave. I'm glad you're thinking this through before you find yourself in hot water. Many people jump into relationships before considering the broader implications. And some, like your friend, pay a big price.

Many people would tell you to steer clear of dating anyone at work, just so you don't run any risks to your professional reputation. But it's unrealistic to make a hard and fast rule to never, ever date a coworker. I mean, where else do you spend that much time with people? It's very common for people to meet and fall in love at work, even if it isn't the best career move.

When you're dating someone you work with, other co-workers and managers may presume that you're favoring them, sharing information or any other host of career-killing infractions. Even if you're not doing these things, some people will still consider you guilty.

In the interest of mitigating any career damage, your best approach is to tread lightly. Look around and see if there are other people in your organization who openly date. If so, has this impacted their ability to advance? Has the rumor mill made headlines out of their relationship?

If you aren't her superior, and you don't work in HR or in another position that gives you access to your paramour's confidential info, you might be OK in asking her out. But do your homework first. Check out your company's policy on workplace dating. If there's a rule discouraging it, you have your answer. It's tough to create an awesome professional reputation when you're breaking company rules.

If you have a good relationship with your boss or anyone else in management, bring up the subject and see what they have to say about it. If they've been around for a while, they may have some inside knowledge about other workplace romances.

Just be careful. Maybe it's best to hang out with her in a group setting first to see if she's really all that. Because asking her out, while a natural inclination, can mean more drama than you want or need. Especially if the relationship goes south while you're both still working there.

Molly Luffy, MBA helps people create more career satisfaction and success through her coaching programs and articles. E-mail your career question to molly@jobpromotionsecrets.com