Should you let your children win at board games? Actually, let me rephrase: Should you let your children win at board games if you can beat them at board games? Because, frankly, I lost a startling number of Chutes and Ladders games to my son when he was 5 (but in my defense, there is zero strategy to Chutes and Ladders, and that dude had no idea what he was doing).

On the whole, we’ve yet to establish a consistent routine about this winning-and-losing situation, and my inconsistency is clearly making a tricky situation worse. Sometimes I’ll take a dive in Battleship, levy an off-base accusation in Clue or make a deliberately lousy chess move to let the little people stay a competitive step ahead, and keep the game moving. And then sometimes I’ll decide that I must use this friendly game of Ticket to Ride: New York to teach him that life is an ever-stretching mosaic of boundless disappointment and that he must begin to navigate it immediately by dealing with how I blocked his route from Central Park to Greenwich Village.

There is little rhyme or reason to these decisions, and it depends essentially on how I’m feeling and how snippy he’s been about screen time lately. Sometimes he beats me at things outright, and that’s fantastic. There’s a game called Blokus that I’ve lost, regularly and badly, to a person who routinely puts his shirts on backward and ends 85 percent of dinners by falling out of his chair. I don’t mind losing to someone who was better than me, which is, incidentally, what I thought after pretty much every Little League game.

But I should have established some system for such games, particularly back when I maintained the ability to keep an upper hand at some of them. Because with my kids now 14 and 6, I’m pretty sure it’s contributed to this curious result: We are really bad at losing.

We are bad at losing board games. We are bad at watching the Cubs lose on TV. We are bad at losing karate competitions. We are bad at losing backyard cornhole games to Dad. We are bad at losing presidential elections (okay, that one’s true for everyone). We are bad enough at losing that last week I caught both kids cheating, independently of each other, attempting to peek in a game that requires some players to keep their eyes closed. They cheated in different manners. One covered his eyes with his hands but spread his fingers apart ever so slightly while the other just went with the ol’ fluttery-eyelid approach. (For the record, I caught this because my role in the game allowed me to have my eyes open, where I could easily keep an eye on my shady, nefarious offspring.)

Needless to say, this resulted in a lively and colorful series of discussions about fairness and ethics, and why we won’t be playing the Werewolf game in the next six years. I think I got the point across, which was weird, as I had to do so in a game involving werewolves and seers and robbers.

Most children are maniacally driven to win, of course, and I’m certainly not raising the only two shifty-eyed tricksters in town. (Do not get me started on the kid down the street and his super-questionable approach to Super Smash Bros.) But watching your children cheat in front of you has the curious effect of making one rethink his entire approach to games, sports and life in general. I don’t have the slightest answer for how to handle these situations when you’re playing games with kids, and anyone claiming to is trying to get you to either click on a headline or invite them to share their hard-line old-school Strict Parenting Techniques at a conference. And I grew up a Cubs fan, so I was genetically preprogrammed to deal with loss — shapeless, overwhelming loss.

But I do wish I’d established some plan years ago before we first cracked open the Mouse Trap (which is, incidentally, the worst board game of all time), instead of trying to develop a strategy for dealing with competition — and loss — on the fly. I do have a strategy for what happens when I catch them cheating, though, and I’m happy to report the bathrooms are clean.

You can find Jeff Vrabel, a writer, @jeffvrabel and on

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