The Deal with Playing Chess in Union Square against Those Chess People

Okay, glad you clicked on this! The boring decoy title was just to throw people off. This is actually a blog post full of sex tips, based off of my own raunchy personal experience.

Ha, kidding. It’s actually about chess. Let’s get into it.

I’ve been living in New York City for about a year now, and noticed a phenomenon here that I haven’t noticed in San Francisco, Chicago, Houston or any other major city that I’ve lived.

In certain parks - such as Washington Square Park and Union Square - there are a bunch of men that sit at chess tables, waiting for people to play them in chess.


I’ve walked by before and always wondered about how these chess games go down, but never really understood.

Here are the basics you need to know:

  • Anyone can play, at any time. If you see a free table - it’s free! I used to think that some of these matches were scheduled. They aren’t, it’s basically a free for all.

  • Playing, however, is not free. Since betting is illegal, you aren’t allowed to bet on the game, but you make a ‘donation’ of $3-5 to play against these chess guys.

  • You can play with or without the timer, so even the most beginner chess players can take a turn at this.

  • Apparently if you win, they will give your donation back. This is basically urban legend. Most of the time they will laugh at you when you ask, and not give your money back.

  • It will be really hard to beat them. Good on you if you’re able to!

  • Some of these people will offer an option for a lesson. If you pay around $20, they’ll teach you whatever you want for a half hour.

I learned all of this yesterday morning, when after discovering spiders in my bathroom, I fled the apartment and bought a Starbucks drink so I could use the Starbuck’s toilet instead. I decided to wander around the city on an empty Sunday morning and found myself in Union Square.

Maybe it was the caffeine from my Pink Drink, or my newfound desire to stay out of my apartment, but I decided to go over and test my luck in chess.

I settled down in front of a man - who, when I asked him his name, told me that it was “Mustache” - paid him $5 and we began the game.

I asked if he would give me tips as we played, and he assured me he would.

I started with my typical move, using my knight (or as I call it, The Horsey) to move around the board.

I used to do this for a couple moves, because I thought it was fun. Mustache explained, very nicely to me, how this was setting me up for failure later in the game.

Apparently you’re supposed to move your pawns out early so you occupy a good amount of space on the board. And my method of moving my knight around because all my other pieces could stay ‘safe’ while the horse killed pawns…wasn’t very effective. The more you know, hahaha. And to think I was in Chess Club back in Middle School…

We played for about 10 minutes, and Mustache gave me tips along the way. Make sure you balance the amount of pieces on light squares and dark squares. The rooks work well as a pair together to trap a piece. Make sure your bishops are being utilized, they can completely cross the board.

I ended up, obviously, in check-mate, but it was a fun 10 minutes.

So to anyone - with cash on them - that finds this whole public chess scenario intriguing, I suggest you check it out! It’s a nice thing to do: give a little money to someone in need, learn a few things about strategy, and maybe even get a brief history lesson. (Mustache was explaining how certain moves in chess are named after real life Roman battle strategies).

Also, this has inspired me to maybe start up a venture of my own. Should I play The Sims in Union Square? Would people pay me to do that? It’s really the only game that I’m good at. I’m going to think on this.

Until the next one,