Hmm, well I asked my older daughter, who is 29 and a graphic designer, to help me set up a Facebook page for my contracting (construction) business. I'm a nudist, and some of my work is at a nudist campground/resort. At this time she didn't know about this part of my life. She asked me to send example photos of my work. I did, and she set up the page.
Shortly after, my wife (her step-mom) met her for lunch. My wife decided it was time to tell her about our nudist lifestyle. "I KNEW it!!!", she exclaimed. "That explains the picture,"
She went on to explain that among the photos of decks and sheds and kitchen reno's, was a shot of a deck in need of repair. In the back of the shot was my buddy walking away, bare-assed. She and her boyfriend spent days on and off trying to figure out what the hell a naked guy was doing on a deck in a work photo (he showed up while I was estimating the job).
It wasn't a dick shot, but the awkwardness was big for her. We all had a good laugh. I still don't know how that photo wound up in the bunch. I couldn't find it when I went back to find it, and I actually go to lengths to never have anyone in my photos of work, let alone my jobs at the nudist resort.