“Kidding a kidder” (or “you can’t kid a kidder”) means you can’t fool someone who is themselves skilled at deception or joking. A trickster sees through another trickster’s tricks. “Kid” as a verb meaning “to tease or deceive playfully” and it emerged in English slang in the mid-1800s, likely from the noun “kid” (young goat), by analogy, with the idea of playfully “kidding around” the way a young goat frisks about, or possibly from the canting of thieves’ where “to kid” meant to coax or wheedle someone. By the late 19th/early 20th century, “kidder” (one who kids/jokes/deceives) was established slang, and the reciprocal idiom “you can’t kid a kidder” followed naturally. It’s a rhetorical way of saying someone recognizes a con or a joke because they run the same game themselves. It’s a self-aware admission like “I can’t believe he thought that story would work…you can’t kid a kidder” (said by someone who is themselves known for jokes/scams). It can also be a warning or boast, as in, “Don’t try that on me… you can’t kid a kidder” (I see through manipulation because I use it myself).
People kid each other for a mix of social and psychological reasons. It’s often about bonding, with playful teasing signaling familiarity and trust. The theory is that you generally don’t tease strangers. It’s a way of saying “I know you well enough to joke with you” without saying it outright. It’s also about testing and reinforcing relationships. Light ribbing checks whether the relationship can handle a little friction. Absorbing a joke well (and giving one back) proves the bond is solid. Deeper psychology implies that there may be an issue of status and hierarchy play going on. Teasing can softly negotiate social pecking order without the aggression of a direct challenge. It’s often used for diffusing tension as well. Humor, including kidding, lets people raise touchy subjects (a flaw, an awkward moment) in a low-stakes, deniable way. If it lands badly, either side can say “I was just kidding.” As we’ve seen lately, its a trick Tump uses all the time once it’s clear that he’s made a gaff that he can’t double down on. It can also be a form of affection disguised as needling. In many cultures, especially among men or in sibling relationships, direct affection feels vulnerable, so teasing becomes a socially acceptable stand-in for “I care about you.” Inside jokes and running gags mark who’s “in” the group. Kidding that references shared history excludes outsiders and strengthens the in-group feel. There’s also the fact that humans are playful animals and verbal sparring is fun in the same way physical play-fighting is, activating similar reward and bonding mechanisms found across primates (Oo-Oo, Ah-Ah!). The catch in all of this is that it only works when both people read it as play and are not accidentally offended by it. The same joke that bonds two people can wound if the trust or context isn’t there, which is part of why “just kidding” is such a common (and sometimes suspect) escape hatch.
When I was in the business world regularly, we all had our armor on at all times. That made the risks of getting caught out by kidding much lower. We were all big strong guys who could take a joke and, in fact, it was almost a necessary part of the social interaction to be able to get as well as you could give. That has changed somewhat in retirement and in the same way that we do not suit up with our businessman’s armor every morning, and instead wear lots of shorts and tee shirts instead, I think we all tend to go out into the world a little more nakedly and with a little less swagger and need to joust to establish position. I would like to think that that is all less about being old and weary and more about being self-assured and confident enough not to need or care about hierarchy or status. We have all mostly done what we will do in the world and would rather spend our time in pleasant interactions than jockeying for position. When you think about it, men become more like women, not in a pejorative sense, but in the sense that being big and strong simply matters less at this stage of life just as women have often had the benefit of not being protector of the clan that has to maintain a strong outward posture. One of the reasons I tend to think that women make better group leaders in a governance sense is that they have learned the lessons of caring for others as opposed to dominating others and that simply works better for the collective good…at least in peaceful times.
I am much more careful with my kidding these days, especially amongst men I would consider my peers. I don’t want to jostle with them the way I used to in a business setting. I would rather just be friends with them and have us all care about our mutual well-being. I will say that its a lot easier to do that when things are not too roiled in a political sense. Political ideologies do nothing but get in the way of peaceful coexistence for the most part. Once in a while they help bind people, but more often they separate us because the potential for divergent and often strongly held views is so great. When I think about the four neighborhood couples that we interact with the most, I find they all fit into a very different place on the political spectrum and therefore on the kidding spectrum. One couple is quite divergent from our political views and can get quite militant if pushed and so I am careful never (well…almost never) to kid around about things too much and I tend to bend over backwards in the opposite direction, taking on a self-deprecating posture like Buddy rolling on his back. It just makes the interaction easier and more pleasant. The next couple is so non-political as to be incapable of getting offensive and that means that whatever kidding comes their way from me is very light-hearted and jovial at worst. There is no need for positioning with them as they are always so forthcoming and friendly. The third couple is a bit different. The man is closer to the business world and is not yet removed from it like the rest of us. As such, he is the more aggressive kidder and goes at it quite steadily and predictably. It is mostly good natured, but can get edgy at times. I like him so much that I am tolerant of it all and have taken a passive-aggressive approach of telling him outright that I will simply accept all of his criticism as true and valid, all in the hopes of diffusing any combativeness. So far that is working well. It is hard to get too upset with someone when they show you their soft underbelly. And then there’s the fourth couple where she is simply oblivious to the political world and he is clearly on the other end of the political spectrum to us, but in such a simplistic and non-confrontational manner as to be non-offensive. I’m sure I would not like the way he votes, but he is such a hail fellow well met that he is simply non-threatening.
Kidding is an artform and knowing when to kid and how much to kid is certainly something that improves with the wisdom of age. So I would conclude by saying that it may be true that you can’t kid a kidder, but I would also say that you need to consider whether its worth it to kid a kidder. Maybe retirement is a time when we are all supposed to retire our kidding for a kinder and gentler approach to social interaction.