If you think about what happens in a humorous moment or the basis of a joke, there is always an underlying disquiet about something happening, or a state of affairs that puts someone at a disadvantage. This creates tension, and laughter is used as a safety valve for the release of tension in awkward situations of all kinds. It is healthy and restorative to decompress by letting this inner pressure have an outlet, through laughter that shows those present you are not taking it seriously but can laugh it off, so to speak. You are sensitive to the plight of the object of the humor but empathize, and hence you are using the safety valve of laughter to show you recognize the compromising situation and feel for the victim. This is a healthy outlet if not done to mock people or make fun of them in a way to cause pain and suffering, or humiliation, as that can lead to quite serious emotional problems of all kinds, including a chronic self-judgment and self-condemnation that can even result in an early death, actively through suicide or indirectly through developing a chronic health condition, or even an outright decision to leave, triggering a sudden death that might not be understandable to a coroner but is truly an escape from torment.
So the idea of humor as a test of psychopaths is an astute observation. Psychopaths lack the ability to feel empathy for others. They may learn through their intellect, in observing others, what people laugh at and find funny, and go along with the crowd, but will have a hard time empathizing with people naturally on their own and will be more likely to simply criticize or judge someone doing something goofy, unexpected, or through a mistake of some sort. Most people will laugh because it makes them uncomfortable and they don’t want to call the person out, but can’t help needing to release that inner pressure within themselves of feeling bad for that individual. This is why the saving grace is to claim, "I’m not laughing at you, I’m laughing with you," to reinforce the point they are simply feeling bad for the butt of the joke and not wanting to cause harm.
The sociopath will often miss the humor in a situation entirely and if they say anything at all it will be to criticize and judge, and not to laugh in sympathy with the plight of the person who is having a bad moment. So this, indeed, is a good detector for identifying the psychopath as being in humorous situations will put them to the test. It is not a failsafe way to evaluate such individuals because they often learn enough through taking part in things to, in effect, act human and mimic what others might do or say in finding things humorous and will adjust their own response similarly. But an equal value in thinking about this relationship is to better understand the plight of the psychopath and how they have come to be that way.
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