So, my boss... is very old. And very important and influential on an international level. It's amazing that my boss is still working and doing what my boss is doing.
A little background: Our boss is catered to 24/7 due to age and abilities, but also due to the fact that my boss is who my boss is. My boss basically does not do anything for my boss's self... and I don't blame my boss.
While working one day, a higher-up co-worker mentioned to me that their biggest fear is that my boss is going to choke one day on something and keel over. (My boss and this co-worker enjoy a lot of meetings involving food.)
That night, at a work dinner... my boss was at one end, next to said co-worker. I was at opposite end. It is kind of a running joke about how old my boss is, but it is playful and not meant in a serious or rude way. At the end of dinner, my boss starts choking. The entire table goes silent and none of know what the fuck to do. Here I am, a complete schmuck, at the other end of the table and I am fucking crying laughing (but of course, trying my hardest to hold it in). Luckily, boss is old and I was at other end of table. So for the entire time she is choking/coughing, we are all dumbfounded (Do we start Heimlich? WTF is actually happening?) My boss was giving us no signs as to what was going on or if my boss needed help.
So - I look like a complete fucking asshole because I am laughing trying to hold it in in front of the co-workers at my end of the table and I kept trying to say... I'm not laughing at the situation I'm laughing at something else. Because the real reason I was laughing was because my co-worker made the comment earlier that same day about my boss choking and keeling over while out at a meeting. And it was potentially happening at that very moment. So, I was actually laughing at the irony of the situation and not my boss actually choking/coughing.
My boss ended up being fine, getting over a cold and I guess got a little dry in the throat. But it was terrifyingly hilarious and that was probably my biggest "I should not be laughing" moment to date.