When Should I Stop Letting My Kid Win?

Advice from a professional baseball player, a board game designer and others.

LetKidWin

When you’re a dad, parenting questions often come up that you struggle to find an answer to. Since other parents are the worst and Google will send you down a rabbit hole of paralyzing, paranoid terror, we’re here to help by putting those questions to the experts. This is “Basic Dad,” an advice column for dads who feel stupid about asking for basic advice.

The Very Basic Concern
It was about a month ago that I first introduced my toddler to the game Candy Land. At first she was really excited to play — it’s a cute, colorful game perfect for her age. But instead of doing what I figured most parents would do and let their kid win, I decided to play it fair and if I won, I’d model gracious winning for her, figuring she would benefit from the lesson of losing.

Well, my brilliant forward-thinking parenting idea blew up in my face. I did win Candy Land and was as gracious as I could be, but my daughter broke down in tears and said that she hated that game and vowed never to play again. And true to her word, in the handful of times I’ve suggested to play it again since, she declines saying, “Daddy, I don’t like that game.”

It seems like it’s probably a good idea to let your kid win, at least some of the time anyway, so for any games going forward — except Candy Land, of course — I plan to let her win some, and then I’ll win some. That much I’ve figured out, but how long do I keep this up for? Can I ever competitively play a game of Monopoly or basketball or anything with my kid? At what point can I actually play with them without stacking the deck against me?

Basically: When do I stop letting my kid win?

The Expert Advice
David Gerrard, father of two and a board game designer at Junk Spirit GamesTo harness a love of games in your kid, one thing you should do is cheat. I have a 10-year-old and a 12-year-old, but when they were little — before they knew what cheating was — I would cheat. If you’re playing a game like Candy Land for example, you have a deck of cards and you pull the top card and it tells you which spot to go to next. So, what I would do is, I’d watch my children’s attitude during the game, and if they got too discouraged because they got too far back, I would let them know that “you never know what could happen,” and when they’d look away, I’d manipulate the deck of cards so that it would help bring them ahead. Just enough to bring them back into the game though. Or, if they were way ahead and they were getting cocky, I’d manipulate the game the other way. Toward the end of the game though, I’d stop doing that completely and the game would just unfold as it did from there.

To give you an analogy, the best way for you to learn tennis is to find someone who’s just above your level and play against them competitively. If you compete with someone who is way below you, you’re going to hold back and not learn anything. If you play with someone way better than you, you’re going to give up because there’s no way you’ll beat them. So by keeping the game competitive, you keep the intensity there and you keep your kids focused on the game, and by doing that, they learn more.

The thing with games is that in that two-hour time period, you’re letting your child set a long-term goal in winning the game, and to achieve that goal, they also have to complete a bunch of short-term goals and achieve those, too. And by playing games, either winning or losing, you’re setting them up to be a winner over time. They get used to setting goals and smashing them so they can win overall.

For my girls, I stopped cheating at the game when they started to realize what cheating was. Then I started to talk about the integrity of the game, and how to maintain the integrity of the game, no matter what it is. I didn’t just begin to full-on compete with them though. Instead, I started to play what I call “open handed” and by that, I mean that every time I played my turn, I would explain what I was doing. So if we’re playing Risk and I take Australia, I’d explain why I’m taking Australia. Like I’d tell them that I’m taking Australia because in two turns I plan on attacking this front here in China. Hopefully from that, they can then take in that information and strategize with it. The goal being that, over time, I can create someone who is as good at the game as I am.

Theresa Russo, PhD in human development and family studies: This is something that’s going to be a bit age-driven. I’d say that for kids in preschool and young, school-age kids, that occasionally letting them win, though not every time, isn’t a bad idea because they’ll get discouraged if they don’t. If they’re always winning, however, that can become problematic, especially with their peers, because they expect to win and they don’t know how to deal with not winning.

You also have to model both good losing and good winning to kids. So sometimes it’s important that the parent wins and they model what a good winner does by not gloating or being obnoxious. Then they also should let the child win sometimes so they can model what good losing looks like. That way, kids learn that it’s okay that sometimes you win and sometimes you lose.

When you get into adolescence and young adolescence, like 12 to 14, it’s a different kind of thing. Then the lesson is that you have to work really hard to be good at something. Generally by that age, the child will have found something that they’re passionate about — if it’s a game of skill like chess or basketball, and they’re trying to become competitive at it, then your goal is to help them master those skills. Also, if they’re passionate about it, the goal is that they want to play because they love the game, not because they want to win. Now, this may take some transition, and you’ll still want to be sure you don’t completely discourage the child, but by no longer holding back, or at least not as much, eventually they’ll be able to become more competitive at the game. Over time you may not even need to let them win anymore.

Rick Greene, father and former Major League pitcher with the Cincinnati Reds: In order to develop a well-rounded child, it involves many lessons of success and failure. If your child always wins, there’s a good chance they’ll have a drastic reaction to a loss. If they have continuous failure, their self-esteem will suffer. For me, the general guidelines I have are that games like Chutes and Ladders or Candy Land — games which require very little skill and are more about chance — I’d never let my child win, as I believe the playing field is already level.

In games of skill, like one-on-one basketball or ping pong, I still go with the theory of not letting my child win, but I may not play at 100 percent the entire game. You may also set a handicap for the better player before starting, like the child has to get to 5 and the parent to 10 to win the game.

It’s important to note that no matter who wins, each player acts accordingly after the contest. Talking to your child about why they lost and how to handle it will go a long way with coping with defeat. “Humble in victory and gracious in defeat” is a great motto to live by.

Kimberly Bell PhD, clinical director of the Hanna Perkins Center for Child Development: I wouldn’t necessarily say that a parent should let their child win. For example, if it’s a game of chance like Candy Land, you would monitor the kid’s frustration level. So in that game, there are pieces that can send you backwards, and if a very young child is struggling too much with that part of it, you can play the game by taking those pieces out. For something like chess, what might help them win is for you to point out when the child is about to make a move that isn’t so great and suggest to them something else. That way, it can be a teachable moment instead of you yourself making a mistake so that they win, because kids will pick up on that. For something like basketball, you might play on your knees so that you’re at the same height as your child, or maybe you’ll play HORSE and give the child easier shots to make. These are ways to even the playing field but not outright cheat in their favor.

If you do things in this way, it’s not as though you ever outright stop letting them win, you just continually adjust your skill level to their current skill level. Eventually, they will grow out of the need for those adaptations. Eventually, you’ll be able to play at your full level whatever the game is and by the time they’re in junior high or high school, they may be better than you at a given sport or game.

One thing to be mindful of, though, is that fathers have to remember that the moment their child surpasses them — that moment when a child genuinely wins on an even playing field — they have to show a great deal of pride, because kids will feel guilty the first time they best their father. This moment doesn’t usually occur until adolescence, and it’s a moment where the child separates a bit from the adult authority figure and finds their own identity. It’s a rite of passage into [adulthood]. So it’s important that the father shows that they want their child to get stronger and better and that this is a source of pride for them. It’s a high-five moment for sure.