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 behaviour 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 behaviour.

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. 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.



* Emily Yoffe is an advice columnist, using the name Prudie.

Washington Post/Slate