Dear Prudence: I was obsessed with a young woman I mentored.

Help! I Sort of Stalked the Young Woman I Was Mentoring.

Help! I Sort of Stalked the Young Woman I Was Mentoring.

Advice on manners and morals.
June 5 2014 8:00 AM

Office Stalker

I wouldn’t leave alone the woman I was mentoring. Can I still fix things?

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.

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Dear Prudence,
I am a professional male in my late 50s in a large corporation. About three years ago, I entered into a professional mentoring relationship with a junior female employee who was then 24 years old. She has told me that my advice and guidance have been tremendously helpful in her professional growth. For most of this time we worked in different locations and our communication was usually via email or phone. Not long ago we agreed to meet outside of work for dinner in order to get to know each other better. Before the dinner took place, I suffered a major heart attack and almost died. My recuperation was rapid and we had our dinner three weeks later. This meeting was like an electrical charge to my system, especially in the aftermath of a near-death situation. After that night, I could not get her out of my mind and developed a very unhealthy infatuation with her. Compounding the problem, she was transferred to the same building where I work. I tried to move our relationship to a much more personal level (I never said anything of a sexual nature) and the harder I tried, the more cool and distant she became. A couple of weeks ago she told me she was going to be out on an assignment. In my paranoia, I thought she told me that only to avoid seeing me. That afternoon, I prepared some professional-development material to leave on her desk. When I went to her office, she was there. I gave her the materials and left. The more I thought about it, the more hurt and angry I became. I sent her a text asking if she thought it was time for us to end the mentoring relationship. I told her that while I may not have been in love with her, I was definitely in love with the idea of being in love with her. She told me that she agreed we should end it and she promised to keep the entire drama between the two of us. Believe it or not, I’m one of the good guys who just happens to have made a terrible mistake. Is there any way I can repair this relationship, rebuild her trust, and regain her friendship, or should I cut my losses and let it go?


—Feeling Regret

Dear Regret,
The word mentor comes from The Odyssey; Odysseus asks his wise friend Mentor to watch over his son when he leaves to fight the Trojan War. However, were Odysseus to have discovered that his trusted Mentor turned out to be a letch, he surely would have used his martial skills on him. As long as we’re talking about the Greeks, you allude to a reason you went so overboard so fast for your protégée. There you were, a passenger on a ferry across the River Styx, and just before arriving at your final destination, you beat it back to the living. If you are being truthful when you say your recent behavior is out of character for you, it may be that in your rush to recover, you haven’t really dealt with what the fact that you almost died. But that still is no excuse for your behavior. Helping guide the career of a promising colleague is a wonderful thing, but there are many ways for the relationship to turn rancid, and having the older partner develop a romantic interest in the younger is at the top of the list. Your silly excuses to drop materials on her desk, your declaration of loving the idea of being in love with her, makes me imagine the letter she might write me. It would be about the older guy at work who had been so proper and professional and has now become her stalker. Please just leave her alone. If you must have contact for work reasons, be cordial and professional. The less you see of her, the easier it will be to regain your mental health. In order to speed that process, find a therapist to talk through your medical crisis and how unmoored you became in the aftermath. You mention no wife or girlfriend. If you’ve been lacking in romantic partners, this second chance at life in the second half of your life is a good time to find someone who shares a mutual desire to be together.


Dear Prudence,
I have been at my job for several years and am planning on leaving in August to begin graduate school. Everyone at my small company knows I am leaving except my boss. Normally, I would want to give him as much advance notice as possible, but my work is in politics, and last year I made an informal commitment to stay through the November elections of this year. I had considered deferring graduate school in order to keep my promise, but was offered a scholarship that can’t be deferred. The problem I have now is: I know from my mentor and superior at the company that as soon as I tell my boss I plan to leave before November, he will fire me. I can’t afford to be without work for the three months leading up to grad school. I feel terrible about waiting until the last minute to tell him, but I also know he understood last year there was a chance I couldn’t stay. Do I tell him now, and try to find some kind of job to make ends meet until school starts? Do I wait, and live with the guilt? I have the blessing of my mentor to stay as long as I need to, but I feel like I’m taking advantage of my boss, and am worried about burning bridges professionally.

—Giving Notice

Dear Giving,
The real problem here is that the boss is either oblivious to what’s going on in his own shop, or people deliberately keep him in the dark to make life more pleasant. Your choices are to tell the boss right away and get fired, or stay on and collect a needed paycheck. Either way, from your boss’s perspective you’ll have torched the bridge, so I think that tips your decision in favor of doing what’s best for you. To make sure you are legally in the clear, I spoke to employment attorney Philip Gordon, who said that since your agreement was informal, your leaving is not actionable. As he noted, if the boss were to have decided to suddenly let you go, the informal agreement he made wouldn’t have protected you. You have the kind of mentor who’s looking out for you so much that he or she will presumably be the target of the boss’s ire when you leave. I assume your mentor wrote a recommendation for you, so can’t plead ignorance of your plans. You work in politics, so you’re well aware, as is your boss, that your field ain’t beanbag, nor tiddlywinks, nor Parcheesi, nor even Go Fish. So do the best job you can for your firm, then move on knowing there was no ideal choice.