Dear alizee207:

“or letting things unfold naturally and hoping he’ll make a move”- nothing much happens naturally in our complex, modern human society, especially in the workplace. There are so many considerations: workplace rules and regulations, stated or inferred, workplace politics, concerns regarding future promotion, work gossip and whatnot.

As a matter of fact, I know of a handsome young man in a managerial position who was involved in a short love affair with a woman who is not a manager. Their short relationship unfolded very naturally, leading to a thorough investigation that resulted in the man getting fired (the woman received a written warning). He’s been looking for another job for months and is worried that his passionate affair at work is the reason why he has not been considered yet for a new job.

Because the context you met this man is the workplace, if you were to approach him, you will have to do it in such a way that he will not feel threatened for one, that is, you don’t want him worried that other people can hear what is said or can observe awkward body language between the two of you. If you talk to him about a possible get together, a date or a relationship, suggest it in a business like manner, not emotionally or flirtatiously. Present it to him in such a way that his answer right-there-and-then is not required, in such a way that he can comfortably withdraw, but clearly enough so that you will know his answer.

anita