What’s the most awkward “not reading the room” encounter you’ve ever experienced?

I work for a company that does state to state residential moving here in the US. The other day my boss and I were packing and loading our customer’s furniture into the truck. The guy was out there us helping as well and of course we’re all making small talk. My boss has two kids.

At some point my boss asks our client whether him and his wife have children and he replies “No, we actually decided that we won’t have children.” My boss replies something like, “Wow, really? Hm. Well you guys are still young, I have a feeling your wife will change her mind in a few years.”

The customer kind of chuckles and says “Haha nope, we’ve thought looong and hard about it.” My boss goes “Okay, I’m gonna call you in five years and ask you again, you might have a different answer!” At this point our client is noticeably getting a bit irritated with my boss egging this conversation on and just goes silent after that.

In my head I couldn’t help but think “What if they possibly have some issues with having children and he’s just trying to avoid the conversation?” I really wanted to tell my boss to just shut the f*ck up but obviously I can’t, so I just stood there silently shaking my head in disapproval. My boss (unknowingly) completely came off as an insensitive jerk off.