Q.: I am a 27-year-old man interested in a woman at work. We are almost the same age, and she is attractive. Our company does not like its employees to date each other. What should I do? I like my job, and I like my female co-worker. How do I ask her out on a date without risking my job? – Young in Love, Chicago
A.: Check to see whether your company has written guidelines about staff members dating each other. If so, recognize that if you choose to ignore those guidelines, it could rightfully cost you your job. If the idea of not dating at work is more of an implication than a rule, you may have some leeway. Not much, though. The culture of an organization is the blood that pumps through its veins. Part of the reason that the company may discourage employees from dating is that such relationships can be distractions.
That said, if you feel the urge to date this woman so strongly that you are willing to risk the potential repercussions, invite her to go out with you on the weekend. Get to know her outside of your office. If you two like each other, remain discreet, which includes not texting, flirting or spending time together on the job. If you are able to do your work without being affected by a potentially budding romance, you may be OK.
Eventually, though, if you two become a real couple, you may want to tell your bosses so that they don't feel duped when they find out.
Lifestylist and author Harriette Cole is president and creative director of Harriette Cole Media. You can send questions to firstname.lastname@example.org or C/O Universal Uclick, 1130 Walnut St., Kansas City, MO 64106.