Success Through Confidence Series Part 30: How To Ask A Co-Worker Out

You think you’ve met the man/woman of your dreams – and they work in your office. Some people say that it isn’t wise to mix business with pleasure. But if works for you and your both have feel a mutual connection, approach it with these pointers in mind:

1. Check your corporate policy. Is dating a co-worker prohibited altogether? If so, you are jeopardizing your job. Other companies have policies that allow co-workers to date as long as both parties sign a "Relationship Agreement" release to abdicate liability.

2. Take it outside. Try to organize a group outing or event, and invite the co-worker you're interested in. If she accepts, you're already a step in the right direction. If not, please don’t force her. If she isn't interested in a coffee outing after work with the gang, chances are she's even less inclined toward dinner for two. Take the hint.

3. Ask only once. If you do hit it off outside work, now is the time to venture an offer for a one-on-one outing. Keep the conversation light, and suggest something casual, like dinner or a movie. If he says no, do not ask again later. If he seems a little hesitant, take that as a no-he may not want to hurt your feelings, and may make excuses. Drop the subject and hang on to your dignity. Groveling is not attractive. Remain friendly.

4. Think hard-you still have to work with this person. If things go sour (or go nowhere), you still have to see and interact with her daily. Be prepared for that before you start, and adopt the attitude of maturity.

5. Choose one. If you like one person, that's great. Go for it. If you're planning to systematically ask out every person you work with, you deserve to be fired.
Bear in mind that you're always opening yourself up to harassment suits and even termination. Handle it correctly, however, and workplace dating can lead to great things.