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A few months ago, I joined a chess academy which divides its members into groups of ten for the sake of coaching them efficiently. Mine had eight men and two women with ages ranging from twenty to forty. I became friends with one of these ladies who is married and has a two year old daughter. Most people in our course (including me) find her extremely attractive. Last week, the instructor organised a blitz chess tournament within our group. She and I were drawn to play each other in the league stage. Before the game, there was a bit of playful banter between us but at no point did I consider the outcome to be of any importance. During the game, I played a good move which she appreciated. That somewhat charged me up and I pulled out my best game which she unfortunately couldn't match. She congratulated me quite warmly and declared that she was proud of me. There was nothing to suggest that she was upset. As luck would had it, we both won our remaining matches and qualified for the final round where we are slated to face each other again.

The problem is: She has started believing that I am the better chess player. I hate to see her low on self-belief. I am afraid she might lose tomorrow's game as well. How can I raise her spirits in case I win without feeling guilty myself?

Please note:

  • We share a platonic relationship. She seems to treat me almost like a child as she is much older.
  • I am still a student (Mathematics major) while she is a teacher (teaching biology).
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    I would like to earn her admiration and at the same time make sure she doesn't feel embarrassed or disheartened if she loses the second game as well. – user16129 Apr 1 '18 at 13:06
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    Does she seem bothered by the idea of you being a better player? Is it an unreasonable belief? Is it possible she is recognising your skill level in a rational way that doesn't upset her? – Kat Apr 1 '18 at 23:19
  • @Kat There is nothing to suggest that she was bothered by the first defeat. However, losing in public twice to someone who is a friend can be embarrassing at times. What should I do in case I win again? – user16129 Apr 2 '18 at 5:13
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    Just play normally, that is the way should be. She won't learn anything if you let her win. I remember playing with my dad every night and losing until one day I finally beat him and went upstair running to my mom to let her know. One of the best day of my live. – Juan Carlos Oropeza Apr 2 '18 at 16:31
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    Stop assuming that her emotional response is something that you are responsible for. Just play a fair game. – swbarnes2 Apr 3 '18 at 21:37
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I agree with what others have posted on letting her win intentionally, which I feel will just hurt her even more.

However, despite that you may be much better than her, I believe there are surely things that you can learn from her.

So when playing a game, how about trying to observe more of the "learning points" or some "different perspective" you learnt from her? I feel that even though one might be very good in a game there is always something to learn from the other.

And when you found the "learning points", do point it out and even remark how you are learning from it.

For example, after the game:

Thanks for the game. Just now there was a move that I didn't expect and have stumbled for a while. That's really something I might borrow and use next time I play. It's something new for me (learning point). But if in the next few steps you have played [like so and so], I'd have probably been in deep, deep trouble (advice + appreciation of the learning point).

Of course, you have to be genuine about the learning points you discovered. And if you really didn't find anything, how about something beyond skills, such as her attitude and/or learning spirit?

Letting her to know how much of the positive impact she has left to you, I believe will raise her spirits.

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I wrote this answer when this question had the title "Letting someone win a game?" Then someone changed the title and the question.

Don't let her win!

Most people don't like to "win" because someone else lets them win. It feels like being cheated. And it feels like "this guy must really think he does me a favor by letting me win".

And people who play games and other players regularly know what moves another player does or doesn't do. In this case: Maybe she would know that you let her win or at least she would guess that you let her win. That won't make her feel good.

In many games there are options of a handicap. If you feel you are better than her offer her a handicap - and then try to win. Then the game is fun for both of you.

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    Unfortunately, this is a game organised by an academy. Handicap isn't an option. – user16129 Apr 1 '18 at 13:08
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    On top of that, answering the original question, in its form, was really a bad idea I believe. It wasn't on topic. And now, it doesn't match at all anymore... Is it worth being TFGITW ?... ;) – OldPadawan Apr 1 '18 at 15:57
  • @OldPadawan: I think it's a good question to ask if it makes sense to let other people win. I was a few times in the situation that other people let me win. I didn't like what they did and didn't play with them anymore. – user8838 Apr 2 '18 at 2:59
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    @Edgar : it can be a good question but it's not the point here. Q was closed quickly because it was "off topic". OP followed the advice and edited. Q was re-opened. Now, it's "How can I raise her spirits in case I win without feeling guilty myself?" and it's not about let her win or not, it's not a polling question anymore. It's not about a win/lose situation and that puts this answer, even with UV, a LQA that doesn't answer the Q. Now, it's only my POV: but despite the fact you'd like to share your own experience, it has to be part of a targeted answer that takes the final Q into account. – OldPadawan Apr 2 '18 at 7:19
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I'm an avid chess player as well, and one of the things that helps me to feel better about a game I lost is to have my opponent show me the missteps I made, as well as the "star moves" that I made during the game. If she's serious about getting better, this is the move to make.

For the uninitiated, this is a common practice in the chess world known as the post-mortem. A post-mortem is a chess game analysis that takes place immediately after the game's conclusion. Since formal settings for chess almost always require that both players keep a record of all of the moves made during the chess game (and give leeway for personal notes and analysis on the score sheet for later use), it is very easy to talk to your opponent about how the game could have gone better.

A good way to start a conversation about having a post-mortem is to just ask. She's clearly interested in improving, so there's no harm in pointing out where she needs improvement. Make sure to be a source of encouragement for her as she improves.

Hey, that was good game. You improved quite a bit in a few areas since last time. I also noticed that you had me a bit trapped at a few parts, namely at [position], and it seems like you have gotten better at putting me in that type of position since last time. I was able to take the advantage back when I noticed you had a weakness in [position or her following move]. If you improve on these parts, I'm sure it will get a lot tougher for me in the future. What do you think?

Of course, edit the discussion as needed. If she didn't trap you at all, for example, you could point out that you were able to see her plans and push past them.

In this particular scenario, with a formal chess academy playing chess together in small personalized groups, the best answer is the post-mortem, with follow-up and encouragement as the games go on and her skill improves.

Best of luck!

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A game like chess is about winning - and losing. It's not about "self belief". It's about focussing, thinking hard, and doing your best to win, to draw if the opponent is good, and make it as hard as possible for the opponent if they are too good for you.

A normal adult, married woman with a child isn't going to lose her "self belief" over losing a game of chess. Are you the better chess player? There's nothing wrong with that, and if she correctly believes that you are the better player, there's nothing wrong with that either. I assume she also believes that she is a better player than the eight others in that event, right?

Now if you let her win, that tells her you think so little of her that you start cheating to make her feel better. That's embarrassing, and likely to destroy a friendship. I'm sure there are women who would appreciate that kind of cheating, but a woman joining a chess academy won't.

Whether you are the better player or not, play your best game. That's what people want, because that's how they learn.

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