Dear Betsy,

I am interested in my supervisor. I think he is interested in me. I can't date him right now, but I am likely to be working in a different location to work in a few months. Then he will no longer be my supervisor.

I sent him a fortune cookie without my name on it stating as in his fortune, "In May, 2008, your life will change in a positive way-you will be able to tell the woman whom you're interested in how you truly feel about her-seize the moment and have the time of your life with her."

Was this okay to do?

Signed,
The Fortune Teller
___________________________________________________________

Dear Fortune Teller,

I love this question. I laughed out loud when I read it. My first reaction? Honestly? Sounds a stunt I might have pulled. But then there were those other reactions. As usual, clear thinking takes time. And as often happens, my first thoughts were less thoughtful and more impulsive than those that followed:

1. Hee hee hee! Ha ha ha! What a great idea. You've figured out a way to test the waters without jeopardizing your job or risking rejection. If the guy responds positively, you'll both have a great story to tell your kids one day. If he doesn't respond, you won't have embarrassed yourself because you can always deny having had anything to do with the mysterious fortune cookie incident.
   
2. Uh oh. I forgot to ask: Is either of you married or currently in a committed relationship? If so, forget what I said above. It's always, always, always a bad idea to get involved with a married man, especially if you're married yourself. Affairs have a very poor long-term success rate.
   
3. What are the rules governing the supervisor/supervisee relationship in your company or profession? And what is the purpose of those rules? For example, in my profession there are strict rules governing the supervisor/therapist-in-training relationship. Those rules were designed to protect supervisees from possible abuses of power or influence by a supervisor. These abuses--conscious or unconscious--are most likely to occur when professional boundaries are breached or compromised by a dual relationship.
   
4. What happens if your supervisor responds positively to your advances, but you don't end up working somewhere else? Are you prepared to live a double life in which you'll have to sneak around and deceive people in order to hold onto your job?
   
5. What if it turns out that the guy doesn't feel the same way as you do and he figures out you sent the cookie?
   
6. How will you keep from feeling one-down in your relationship if you don't get transferred and your supervisor becomes your boyfriend?
   
7. If it doesn't work out between you and your supervisor, how might this affect your work relationship and career?
   
8. Would you consider leaving your job to maintain this relationship?
   
9. Have you considered the repercussions of breaking the rules?
   
10. Could either of you get fired or blacklisted if you were "found out"?
    

Obviously, none of these questions will matter unless the guy responds positively to the fortune cookie. But in the event that he responds positively, I'd want to seriously consider these questions before going any further.

Good luck! No matter what, I think you're a riot. My only advice is to be careful and look beyond your first impulse, as you've challenged me to do with your question. Keep me posted. I'd love to hear how this one turns out.

Betsy