I wonder if this would help...
Timing. The thing that either makes or breaks comedians. Some people are gifted with the natural ability to say the right thing at exactly the right time. Some, however, lack this miraculous talent. I for one am usually the latter.
My tendency to pull out the "too soon" joke is infamous. I notoriously crack jokes inappropriately soon. Luckily, I am learning to filter. Especially around company that's not, well, accustomed to this quirkiness. So I sometimes wonder, what is grace period after a traumatic or embarrassing event? How long until I can publicly laugh about it?
This same question was asked by the producers, writers and actors for Saturday Night Live. Their 27th season aired on September 29, 2001. Only eighteen days after the 9/11 terrorist attacks. The show opened with Rudy Giuliani and firefighters and police officers of NYC, announcing that SNL would continue to air as scheduled. Lorne Michaels asked Giuliani, "Can we be funny?" The mayors response, "Why start now?" It seems that despite the sadness and grief surrounding our nation, SNL's prescription was laughter.
And why not? Haven't you wondered why all late night television tends to center around stand up comedians and their talk shows? After a long day, a hearty laugh can seriously work wonders. But then again, timing. Kidding about something too soon possesses the ability to wreck havoc. Opening fresh wounds. So maybe the saying, "time heals all wounds" is really accurate.
In the end, I still master the too soon joke. And yes, while in the moment everyone is mortified and the air is permeated with awkwardness, eventually you can laugh.