Should I Always let my Son Win?

Should I Always Let My Son Win?

I watch as my son slams his fists on the couch, jumps up and angrily storms off to his room throwing a tantrum all the way there.  
So what was it that made him so mad? Did I tell him he couldn’t have ice cream? No. Did I take away his iPad to punish him for something he did wrong? No. I did something far worse in his eyes…I actually beat him at a game of Monopoly.  
My son is a very sore loser. He is 8 years old, and whether he is playing a board game, video game, or any kind of sport, the possibility that he might lose doesn’t seem to ever occur to him. He’s playing against an adult who is 5 times older than him, but in his mind, he has a legitimate chance of winning.  
I’ve been playing games with my son ever since he was old enough to play them. As you can imagine, he loses a lot. The only times he ever wins are when we play games when winning is all about luck. Board games like Snakes and Ladders, or Trouble. In school, he started learning to play chess against other kids in his grade. He learned a technique that can result in a checkmate in about 5 moves. He legitimately beat me twice with that, but now that I know what’s coming, I can avoid it. So he doesn’t beat me at chess anymore, and he doesn’t want to play chess with me anymore.  
Basically, any time he has ever beaten me, it was because I allowed him to. His gloating sessions that result after his “victories” feel very amusing…and a little annoying. Do you think I gloat after I beat him? I’ve never once shouted “In your face!” or a single “Booyah!”  
The ego of a child simply amazes me. It’s one thing when I let him win at video games on our Wii. He can occasionally beat me legitimately at Mario Kart, Mario Tennis or Super Smash Brawl. But he’s recently discovered how to shoot pool. Of course he’s not very good at it. He can barely hit a ball with the cue ball, let alone get one into a pocket. We play 8-ball, and naturally I could easily sink all my balls before he could sink a single one of his.  
I want him to have fun, so I’ll do everything I can to help keep him in the game…but it’s not easy. I will be constantly missing my shots intentionally, while at the same time trying to set up easy shots for him to do. Then I start getting a little annoyed when he can’t even make those ones. When the game finally comes to an end, and he gets his win, I don’t know how he can’t suspect that maybe I missed 23 shots in a row on purpose. Maybe he does know, but just doesn’t care. Maybe a win is a win to him no matter how he gets it.  
Sometimes, it seems like he expects me to let him win. During the aforementioned game of Monopoly, I won the game because I ended up getting both Boardwalk and Park Place (the best way to win any game of Monopoly as we all know). As I landed on each one, my son begged me not to buy them. Of course, he would have bought them in a flash if he had landed on them first. Then after I choose to buy them over his protests, he proceeds to call me a “meanie”; his favourite word to use when he doesn’t get his way. Then his tantrum came after he landed on Boardwalk (with only 2 houses on it). Despite the fact that he had enough cash to pay the rent, and that he owned everything on the board from Mediterranean Ave. to B&O Railroad, he decided the game wasn’t fair and stormed off.  
That’s when I came to think that maybe I shouldn’t let him win anymore. Perhaps when we play now, the most I should do is just keep the game close. I don’t want to embarrass the kid by running the table when we play pool, or beating him in straight sets when we play Mario Tennis on the Wii. I just don’t want him to get used to winning all the time.  
I really want my son to learn how to lose gracefully. Whether he is playing with me, with his friends, or with the faceless online players on his iPad games, I try my best to teach him the pointlessness of caring about winning or losing in these situations. There is no trophy being given, no prize of any kind. His favourite sport to play is soccer. He’s doesn’t play in a league yet, but he takes soccer lessons, which is essentially just playing lots of practice games with the other kids in the class. If he loses one of these “games”, I have to spend the car ride home listening to him talk about the reasons why he should’ve won, or how unfair the match-up was. He takes these games that are supposed to be about just having fun, and acts like he’s playing for the World Cup.  
I’ve noticed that since I stopped letting him win, he seems less inclined to ask to play with me anymore. So maybe letting your kid win once in a while is a necessity if you want to keep him interested? Just recently though, he has asked to join me for a round of golf that I had been planning with my Dad. My son has never played a game of golf in his life (except mini-putt), so I don’t know how we could play badly enough to let him win that game. Not that we’d want to, considering how much it costs per round. I decided against bringing him because he’d probably just give up after a couple of holes after realizing how hard it is to play. Then he’d spend the rest of the day whining about wanting to go home. I promised to take him to driving ranges until he gets good enough to try an easy golf course somewhere.  
Maybe if I want to make my son feel good about himself, I should just challenge him to a game of soccer. The fact that I’m 42, combined with being 30 pounds overweight and never having played soccer in my life, he would definitely be able to kick my ass.

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