Office Romance: Should She Ask Her Boss Out?

Good afternoon, Ms. MacDonald-

Hope all is well. I love reading your articles, they definitely give me insights on how to move forward with relationships. Today, I need your advice. I am a single mom in my mid 40's and have had no luck in the love arena. I am very skeptical of starting relationships in today's corrupt society.

About a month ago, I went to a job interview and was sparked by the hiring manager; it was like an instant connection. Did not think anything of it afterwords because 99% of those individuals are married. However, within a few days of starting at my new job, I learned that my hiring manager was a single parent.

I feel very attracted to him but do not know if he even looks at me that way. I am one to believe that men are the ones that will make the move, but I am not sure if that will happen. What would be the protocol? What advice can I get from you on how to go about this? I have thought of dropping a line as a secret admirer but do not know if that is appropriate. Perhaps, I should just tell him how I feel but then, what is he going to think of me?

My other concern is how this could impact my job since he was my hiring manager, and I now work under him. Look forward to your words of wisdom and advice. Thank you for your time.

-New Hire

Dear New Hire:

Thanks for the kind words. Call me Terry, please, and congratulations on your new job.

My best advice is this: Don't make a move on him. The rules of romance are quite different when you're at work, especially when the man in question is your boss. It's possible the man is as attracted to you as you are to him; however, it's not in his best interests (or yours) to start something when you're brand new to a company. People are watching you to see how you shake out as an employee, and they're watching him to see if he's made a good hiring decision.

It's possible that months from now, when you're secure in your position, when the two of you have developed a rhythm in your work together, that things may change. But, right now, concentrate only on establishing yourself at the company. It won't be easy, but keep your mind on your work and not on your attraction to this man. It's possible that after working with him for a while, you'll realize you're not attracted much, anyway.

The first thing that popped out at me in your letter was this:

"I am very skeptical of starting relationships in today's corrupt society."

Let's examine this. I've been reading a bit of history lately, and one thing that hits me over and over is the fact that all societies have been corrupt. Read a couple of paragraphs in the Old Testament, and you'll see what I mean.

Evil people have existed since the beginning of time, as do others who operate only with their own best interests at heart. Clearly, you should not start a relationship with anybody like this.

But know that good people also exist. They always have, and they always will.

It really helps to know (put it in writing, please) some of the qualities you'd like in a person with whom you would enjoy a relationship. Often, women will say, "Well, he's got to be no shorter than 5'10, make a decent living, and have a great smile." (Seriously, they say this stuff.)

But a man who's 5'11, makes 150K+ per annum, smiles beautifully, yet can look another person in the eye and lie, who cheats, or is congenitally unable to pick his underwear off the floor probably won't cut it for you.

So, know what you want. What qualities exactly attract you to your new manager? Write them down. Do you want someone who's kind, has a sense of humor, is generous, faithful? Write that down, too.

It's amazing. When you know what you want, it's so much easier to recognize it when it shows up.

Also, since you're skeptical of starting new relationships, please be open to the possibility that so far you have chosen men who will confirm your suspicions by disappointing you. Ask yourself what scares you about waking up to the same person for the rest of your life. Boredom? Losing your identity? Infidelity? Fear of abandonment? Fear of being smothered?

These are all pretty normal fears, but if you can face them head on, you can get around them. If you're afraid of being bored to death, for example, ask yourself, "Is it possible I wouldn't be bored to death?" Think of examples of married or committed couples who still enjoy each others' company for inspiration.

If you can't think of any couples who fit the bill, write a scene between you and your perfect man and set it 10 or 20 years from now. What would you be doing? Would you be laughing? Would you be alone or surrounded by other people who love you?

Read this scene twice a day and bring it to life in your imagination. Use all your senses: What would you see? Hear? Taste? Feel? Smell?

Truly, what the mind can conceive and believe, it can achieve.