Dating Advice From Chess Players

Michael, 31

What has chess taught you about relationships?
It's important to be able to see both sides. Anticipation of someone else's moves not only makes surprises all the more fun, but keeps the connection alive and vibrant. It's also taught me that you can't react only to what's on the table in front of you; you've got to be able to consider the reasons behind the moves. If you don't consider why your S.O. did something, you may react for the wrong reasons.

What's up with everyone playing hard to get? I'm awful at it. Is there any point in trying to get better?
I know! It totally sucks! And. . . oh, I've got to take this. Talk to you tomorrow?

I recently went on a terrible date. It was going badly before the food arrived. How long do I have to wait it out before I can throw in the towel?

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You know, I can't give you any advice on this. I've sat through a few miserable dinners with the worst company I could ever imagine. There was one girl who nitpicked everything on the menu and ordered with a ton of substitutions, but then mostly wanted to eat off of my dish. I made it all the way to the bill on that one. What I've learned since then is: no dinner on a first date! Meeting for drinks is great.

The film Revolver suggests that to improve your chess game, you have to play someone better. Is this true for dating? And how do I go about improving "my game"?
There's a lot of value to spending time with people that inspire you, but a big part of improving isn't to see yourself as worse, but to focus on what you think is good. While there's a great deal to learn from post-game analysis, save that for your alone time. Enjoy your life and enjoy the time you spend with your friends. Good stuff will follow.

I've got twenty bucks and not a dime more — what's an awesome, cheap-date idea?
Go for a night picnic with a star map and a bottle of wine. Grab a dictionary and look up weird words, then try and guess their meanings. Make a chess set out of matching things from around the house. Teach each other something: she could show you how to throw a punch, and you could teach her how to make a French braid. Or vice versa.

My girlfriend never plans ahead — rent money, an umbrella, a condom. Is this something we can work on, or am I doomed to be the one who's prepared for the worst?
In general, yeah, you're doomed. But what about all the spontaneous things she drags you to that you're always telling me about? Like last November, when she hauled you to a Radiohead concert. And it was raining and you didn't have tickets, so you stood on the hill outside, holding a newspaper over your head. Don't you look back and think of how awesome that was?

Joan, 21

What has chess taught you about relationships?
A queen can do anything.

Is playing a game of chess a good first-date activity?
You can learn a lot about a person by the way they play chess. Plus, it's completely acceptable to talk a ton of shit to each other, which is another great way to get to know someone. It's always nice to throw in a little competition: you get the joy of beating them, or are pleasantly surprised and impressed if they beat you.

What's the best strategy for a successful first date?
Strategy suggests an end goal or particular aim, and there's no way to foresee how you're going to feel until after the first date. I say ditch the plan and be yourself, and if they don't like you, they're not worth it anyways.

What was your best date ever?
I've never been on one.

The film Revolver suggests that to improve your chess game, you have to play someone better. Is true for dating? And how do I go about improving "my game"?
I wish I knew. I don't think that can apply to relationships in the same way. You can steal an opponent's strategy in a chess game, but I'd feel funny hitting on someone the exact same way I'd been hit on. It might feel wrong.

I've got twenty bucks and not a dime more — what's an awesome, cheap-date idea?
Forties and the dog park.

I didn't feel like having sex with my boyfriend, and he jokingly offered me a hundred bucks, which I took. Now it's becoming a habit. Is there any way we can keep the arrangement going without our relationship turning into a business transaction?
If you're good at something, never do it for free.

Dan, 38

What has chess taught you about relationships?
It's sadomasochistic. Even when you lose, you can learn. Masochistic, because it teaches you to be assertive, but can also teach you to be too aggressive and overcompensate.

Do you have a secret chess move or signature play that translates off the board into relationships?
Yes. Fool's Mate — you get checkmated in two moves, which means you're easy.

I recently went on a terrible date. It was going badly before the food arrived. How long do I have to wait it out before I can throw in the towel?
Don't throw in the towel. Maybe your date feels the same. Chess players have this saying — nobody ever won by resigning. So don't resign. When going home, then you can laugh.

My boyfriend is great, but he isn't exactly the sharpest knife in the drawer. My friends have commented on this and think he's not good enough, and lately, I've started to get embarrassed. Is the difference in intellect really that big of a deal?
Yep, it is. From a chess player's perspective, you don't want to always strategize; if he can't hold a conversation, it's time to move on.

I am so into this bartender in my neighborhood, but can't find the Hooksexup to ask her out. What do you think about me asking her on a date via paper — like a cute note or something?
No, cause you could come across as a psycho. Show courage and ask her out. Also, try going during a non-peak hour for conversation. One nice thing might be to make her bartending life easier — get her a cute towel.

I didn't feel like having sex with my boyfriend, and he jokingly offered me a hundred bucks, which I took. Now it's becoming a habit. Is there any way we can keep the arrangement going without our relationship turning into a business transaction?
Yeah, try surprising him and giving it up for free.

Charley, 23

Is playing a game of chess a good first-date idea?
Oh yeah, it's great. It takes a lot of time and provides quiet moments for conversation. Also, you can awkwardly stare at the other person while they're making their moves.

Do you have a secret chess move or signature play that translates off the board into relationships?
I sacrifice all of my pawns, which would translate into letting things that I don't really care about slide.

I recently went on a terrible date. It was going badly before the food arrived. How long do I have to wait it out before I can throw in the towel?
As long as you're honest and straightforward and sensitive to the other person, I would get up before the food comes out. But in reality, I'd probably stay for dinner, and then not go out with them again. I wouldn't have the Hooksexup to leave beforehand.

Sometimes after receiving oral sex, I just want to cuddle and pass out, but I feel guilty about not returning the favor. Does etiquette say I should return the favor? Sometimes? Half the time?
As long as you're okay with him passing out next time, sure. You get what you give.

My boyfriend is great, but he isn't exactly the sharpest knife in the drawer. My friends have commented on this and think he's not good enough, and lately, I've started to get embarrassed. Is the difference in intellect really that big of a deal?
Yeah, I'd say it's the biggest deal of all.

I didn't feel like having sex with my boyfriend, and he jokingly offered me a hundred bucks, which I took. Now it's becoming a habit. Is there any way we can keep the arrangement going without our relationship turning into a business transaction?
I say that this is an obvious win-win. As long as everybody involved is happy, there should be no shame in your games.

Interviews by Chantal O'Keeffe. Dating Advice From... appears on Fridays. Have questions for the general public? Send them to .

Dating Advice from Chess Players