So you've decided to transgress the age-old rule of thumb about not dating co-workers and ask that cute girl in the next cubicle on a date. You've heard the nightmare stories of interoffice dating escapades ending in disaster, but you've decided to take the plunge. You're not alone. Office romance among young adults is increasing. Protect yourself, and increase her chances of accepting, by playing your cards correctly.
Review Your Employee Handbook
Some companies have very strict policies about interoffice dating. Some companies have adopted a zero-tolerance policy about it, and transgressions can actually result in termination. In this case, is she really worth losing your job over? Other companies don't outright forbid dating between co-workers, but if the relationship becomes serious, one party may have to leave the company. If things go well with your co-worker, will you be willing to pack it in and find a new job? You also want to be quite sure that the way in which you approach your co-worker does not violate the company's sexual harassment policy.
Leave No Paper Trail
Whatever you do, do not use your company email address to send her a flirtatious message or an email asking her on a date. Some companies are very strict about keeping records of employee emails. If the woman feels threatened or otherwise annoyed by you emailing her on company time for a private matter, she may bring your email to higher authorities. Likewise, you don't want to use the company phone to ring her up to ask her out. This is misuse of company property. Approach her in person, for your own safety. It may take more gumption on your part.
Have a Specific Date in Mind
If you simply approached her and said, "Would like you to go out sometime?" she might say yes just to not hurt your feelings, and then you are left wondering 1) when this hypothetical date will actually happen, and 2) if she was just being polite. Ask your co-worker to accompany you to a specific place at a specific time. For example: "Hey, my cousin gave me two tickets to the theater for this Saturday night. Would you want to go with me?" If she is interested in you but afraid to show you because of office politics, she can accept based on her interest in community theater and give herself time to test the waters with you. If she really isn't into you, she will likely say that she already has plans and won't attempt to schedule another date.
Any woman who values her job might be slightly hesitant about accepting your offer, even if she does find you attractive. Ease her doubts by prefacing the conversation with the fact that you know that interoffice dating is slightly taboo but that you consider her worth the risk. Show her the company's policies about dating to let her know that you've done the homework. Finally, communicate to her that if things don't work out between you two, you are willing to sweep it under the rug and not allow it to affect your work relationship.