Dear Prudence

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.


Dear Prudence,
My grandmother is in her 90s and frail, but her mind is as sharp as ever. She came from one of the wealthiest families in China, and her family was decimated by the Communist revolution. Luckily, my grandmother escaped the brutality because she had just joined my grandfather in Taiwan. There she built a new life amid poverty. Her younger sisters, who were in China, bore the brunt of the revolution. Members of their family were executed, or worked to death, and they themselves barely survived the hard labor and famines. No one has asked any of these sisters for full details about their younger years for fear of dredging up negative emotions. But I feel my generation and the future generation should know what they survived, and who they were. Should I just let the past stay in the past and not trouble a frail, elderly woman, or is there a way I can broach this subject with my grandmother? 

—Family Historian

Dear Historian,
You’re right to be sensitive to the fact that your grandmother may not want to talk about the pain of the past, but it may well be she’s gotten the message that no one wants to hear it and so hasn’t burdened anyone with her stories. Please ask, not only for your family, but for history. Today’s very old people lived through tumultuous times, and we only have a sliver of time left to hear their first-person accounts. You sound like a loving and sensitive grandchild, so if you’re able to bring it up in person with your grandmother, just tell her what you’ve said here. That you know she witnessed epochal events, and you would like to capture her memories. If she agrees, set aside some time and decide how you’d like to record her words, then give her some prompts to get the stories flowing. Understand that her accounts may be scattered and disjunctive, but they will still be gems of insight into recent history. The very old sometimes become time travelers themselves—what they had for breakfast is hard to remember, but the events of that day when they were 10 years old is crystal clear.


Dear Prudence,
I’m a 14-year-old girl and I’m trying to convince my mother to let me get a short haircut. My hair is past my shoulders and I almost never let it out of a ponytail. She won’t let me have it cut past her hair length, which is shoulder length. She’s paranoid about it because she had her hair cut into a pixie cut when she was pregnant with my two older sisters and hated it and thinks I’ll regret it as much as she did. I hate my hair long and I hate hot weather, which makes me all the more hateful toward my hair. She’s being unreasonable about this whole thing and my dad won’t help at all! What can I do to convince her to let me have my hair cut the way I want it, not how she wants it?

—It’s Just Hair

Dear Hair,
Hang in there, Hair, and start saving your babysitting money. In just a few years, you will be going to the stylist alone, and only you will be able to dictate the fate of your locks. I agree that summer is a great time to go shorter, but instead of tussling with your mother over a pixie cut, ask her to compromise. Sit down with her and look through this gallery of delightful bobs, and together pick out a couple that would be flattering on you. Let’s hope she sees that if she lets you get your hair off your back, she’ll get you off hers. As for your father, I imagine that a man with a wife and three daughters, when asked to arbitrate a hair-styling conflict, would rather locate the nearest demolition derby, get a seat in the stands, and enjoy some peace.


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