Dear Prudence

Help! My Boss Sent a Risqué Photo Only to the Women in the Office.

In We’re Prudence, Prudence asks readers for their thoughts on a question that has her stumped. The answer is available only for Slate Plus members.

Woman holding up her phone and covering her face with her other hand; a graphic of a Speedo.
Photo illustration by Slate. Photo by Drazen Zigic/iStock/Getty Images Plus.

Every Thursday on Twitter @jdesmondharris, Dear Prudence asks readers for their thoughts on a question that has her stumped. She’ll post her final thoughts on the matter on Fridays. Here’s this week’s dilemma and answer:

Dear Prudence,

I recently got a picture from my boss of him in a minimal-coverage Speedo that was not sent with any ill intentions, but it was weird enough that I’m wondering if I should say something to him about it.

I am a woman in my 30s, very junior in my career, and he is the most senior person in our workplace both in age (70s) and authority. He also sent the picture to several other young female coworkers, and, as far as I know, not to any of the male coworkers. He’s on vacation, and we know that he is an enthusiastic cold-water swimmer and prides himself on not using a wet suit. So the message, I think, was, “Look at how much fun I’m having on my vacation doing my favorite activity!” But I would NEVER send my boss (or anyone I supervise) a photo of myself in a minimal-coverage swimsuit. We all thought it was kind of icky and weird but nobody said anything to him except “looks like you’re having a great time!”

I don’t think he realizes it crossed a boundary, and I’m worried that calling him out on it could make him feel really embarrassed or accused of doing something sexual when that’s not how he intended it. On the other hand, he could get himself in trouble with things like this depending on who is on the receiving end. Should I say something?

— Unsure

Dear Unsure,

Your boss knew this crossed a boundary. The evidence of that, as many readers pointed out, is that he didn’t send the photo to the men in the office.

If he just wanted to show off how athletic he was still being at his age, he would have absolutely included the men when he sent the photo. He knew what he was doing. — @ladycrim

I need clarity on whether this was via email or text and did he individually send it to people? Somehow that “it’s just fun” sentiment would maybe feel different if it were a group situation vs directly only to women. The intention doesn’t really matter, the impact is creepy. — @kourtbitterly

I don’t believe for a second he had good intentions. He knows you shouldn’t send employees Speedo pics—that’s why he didn’t send it to the men. She needs to report him, so he doesn’t take further on his next vacation. — @Aloe9678

No man who sends a nearly nude picture to only the women who work for him and not the men has good intentions. It would absolutely be reasonable to go to HR about this, possibly with some of your other coworkers who received the text. — @HurricaneMomo

If he only sent this to younger women in his office, not to any male colleagues, then the fact that he was in a speedo was no accident. — @sherri_gill

But even though I was sure this was an intentional, creepy move, as I said when I shared the question on Twitter, I worried about encouraging you to confront him or sending you to HR to report him. Because while you would be completely right to do either of these things, there’s always the possibility of retaliation—especially at a small company, where, for all we know, he and the HR person are best buddies.

A few people who responded validated this:

I reported someone to HR in a previous job at a very small company and it made my life a living hell. zero benefit, but many costs. no good options, but I hope they at least stop giving so much consideration to his feelings! fuck this dude — @linguangst

Yeah, I would focus on making sure she understands it was both inappropriate and deliberate, no question, but there might not be much she can do when she’s the most junior and he’s the most senior. Except look for a new job, which she definitely should. — @KateHarding

Yup, sociology research on sexual harassment suggests that the most common response to reporting it is retaliation without any progress. That doesn’t mean you should never fight back, but you have to be careful & amass support to protect yourself — @ewrigleyfield

So I was intrigued (and delighted) by some of these amusing suggestions that find a sneaky way to put the discomfort you’re feeling back where it belongs—on your boss.

If men get to operate on the assumption of “playful cluelessness” then we should too. Next time (ugh) or when he’d returned, I’d do a cheerful “Hey Earl, I think you may have accidentally sent me a private picture from your vacation! Oopsie! Gotta be careful with these phones!” — @CaseySplinter

Just make a thing of sharing his vacation photos with all your male coworkers since he forgot to include them. — @WiseWyzard

Even better, does the company have social media accounts (or an all-company intranet) and did he send it to someone who does that job? Share it with a caption: “Our Fearless Leader is taking a much-needed break, but took a minute to check in from the field!” — @CAwkward

Those responses would all be super satisfying and are fun to think about, but I ultimately concluded that the suggestion that would be easiest for you to implement and most effective would be to recruit a male ally to address this, either directly or by going through HR.

This is when having a male ally comes in handy. Instead of the femmes who received the pic saying something directly, getting a sympathetic, male third party would absolutely lessen the blow to the boss’ ego and shield them from potential retaliation. — @lenubienne

A reader who didn’t want to be identified, because of her concern that any public feedback she provided could be misconstrued as legal advice, offered additional context via email that explains why using a male ally would be wise. I’m going to include most of her response because I thought it was really helpful:

I have been working in human rights for the past 3.5 years and have read countless cases that have similar fact patterns—often beginning with something like this and then escalating to more aggressive harassment. That is what this is: harassment. Even if the intention of the boss is not to harass, because he is targeting a specific group of people—seemingly based on their gender—it is discriminatory. Remember that the male colleagues get to go through their work days without having to see photos of their elderly boss in a Speedo.

I agree with your sentiment that HR is not there to protect the employees, but this does have to be documented. I would suggest to the writer that they speak to some of the men in the office who are perceived as allies—particularly if any man has expressed disgust or dismay that their female colleagues were subjected to this—and ask them to report the incident to HR. This might seem like it’s “have a man fix it for you” and removes agency from the women in the situation, but by subverting the power that the men in the office hold—reiterated by the fact that they were not subjected to Speedo photos—the women in the office can utilize male privilege in order to create a safer working environment.

It is important that the designated male ally not say, “Hey, the women asked me to talk to you about this” or “The women receiving these photos are uncomfortable, can you talk to the boss for them?” The effort here is to de-center the women as being the ones responsible for the discomfort—because the boss is the one responsible. But by having someone who may have more privilege and power step forward and say, “This makes ME uncomfortable and I think it should stop,” it has a better chance of jarring people into action. 

I hope this is helpful. Good luck!

Classic Prudie

My 14-year-old son recently came across some Polaroid pictures of me that his father took of me back when we were 14 (we have been together for a long time and got married when I was pregnant with my son). The pictures were in an old shoebox filled with baseball cards and other adolescent memories. The problem is that the pictures are nude shots!