Dear Prudence: Anonymous emails are trying to ruin my self-esteem.

Help! An Anonymous Emailer Is Trying to Shred My Self-Esteem—and I Think I Know Who It Is.

Help! An Anonymous Emailer Is Trying to Shred My Self-Esteem—and I Think I Know Who It Is.

Advice on manners and morals.
Aug. 14 2014 6:00 AM

Inbox Bully

An anonymous emailer is trying to ruin my self-esteem—and I think I know who it is.

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.

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Dear Prudence,
Two months ago, after posting a picture to my Facebook in which I said I “felt beautiful,” I started getting email messages from someone I didn’t know that were vicious and cruel. I am chubby, and my harasser wanted to tell me, as nastily as possible, that I was deluding myself for thinking I could be beautiful. Not knowing who was writing to me, I made my Facebook profile more private. But recently a friend suggested that I compare the IP addresses of my harasser to the IP addresses of emails from people I know. To my shock, I discovered my harasser has the same IP address as my best friend’s boyfriend, Adam. Adam lives alone, and based on the times the messages were sent I do not believe another person sent those messages from his computer. Adam has always been kind to me, and until my discovery I thought he was my friend. His behavior makes no sense, and I don’t know what to say to him or to my best friend. What should I do?


—Confused and Hurt

Dear Confused,
I find myself hoping that Adam has a tendency to lose count of his drinks. It’s no excuse, but if late at night the Mr. Hyde side of Adam seeks to express itself, then at least there’s a proximate cause for his venom. But if Adam just likes to vent his free-floating hatred under the guise of a false identity, he is a major creep. Just to make sure you weren’t going off on a digital tangent, I spoke to some people on Slate’s technology team and they said that identifying an IP address can help point you toward a suspect, but keep in mind your evidence is not conclusive. They also suggested that you do as broad a search as possible of the IP addresses of your correspondents to make sure you’ve turned up a singular match between your tormenter and your friend’s boyfriend. If you remain convinced, I think you should first talk to Adam, then tell your friend. Don’t call a solo meeting with him—you want an easy way out if things get even weirder—but next time you’re at a social event together, pull him aside and say you’d like a word. Explain that recently you were getting a series of abusive email messages. So you did some investigating and were disturbed to find that the IP address of your new correspondent was the same as his email. Then fall silent and let him respond. If he indeed is the culprit, let’s hope that he owns up, abjectly apologizes, and says it will never happen again. If so, tell him that obviously you have some thinking to do about your friendship with him, and this also complicates your friendship with your best friend. Say you are going to tell her, but you will let her hear it first directly from him. If he denies knowing anything about it, then say while you think the evidence is strong, you accept that it remains a mystery. Add that you’re going to let your friend know about your conversation. When you tell her, acknowledge that this is putting her in a difficult situation and that there is an element of doubt, but that you felt you needed to say something. Take comfort that Robert Louis Stevenson had some pungent observations about the (possible) Adams of the world: “I learned to recognise the thorough and primitive duality of man; I saw that, of the two natures that contended in the field of my consciousness, even if I could rightly be said to be either, it was only because I was radically both.”


Dear Prudence,
Earlier this year I met a lovely woman and our chemistry was off the charts. I’ve been single the better part of a decade, she and I are in our 50s, and we both recognize how seldom one finds such a connection. I might be what marketing folks would describe as “generously appointed.” The first time she saw me naked she gasped. After our first afternoon in bed she was in pain for several days. This was a new experience to each of us. It quickly reached the point that she became fearful of intimacy. She’s since seen several doctors, only to have them confirm she is not ill and has nothing organic amiss. She wants to have what she calls a normal sex life with me, that is, intercourse as she has always known it. I’ve suggested therapy or a specialist, but she says the problem is not in her head. I believe that her reaction is now reflexive, but can be addressed. For all the men who think they would trade places in a heartbeat, I’m a guy who has found a woman I would love to get smaller for.

—Big Red

Dear Big,
Before I get to you, let me first make an aside: “Ladies, I’m sorry, but my privacy policy means I cannot put you in touch with Big Red.” You’re not just knocking at heaven’s door, you’re splintering it. I hope your letter is received with gratitude by less substantially endowed men; here is testimony that there are women who run screaming from the big kahuna. Though you aren’t being cocky about your equipment, it’s unlikely that therapy, at least of the head-shrinking kind, is going to do much good for your lady love. The issue might be more about technique. This sex toy website offers a good summary of the most salient advice: foreplay, lots of lubrication, slow pace, and position. Arriving at an approach that doesn’t send your friend diving bottom-first into a tub of ice should be a highly pleasurable exploration for the both of you. But if she’s just hung up on your less-hung predecessors, then you will eventually have to find someone with whom you are a better fit. (And gentlemen of more average proportions, sorry, but I can’t put you in touch with Big Red’s friend.)