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