This week, I’ve been playing a lot of over-the-board chess. It’s been nice to find that my win rate is much higher when I’m playing with physical chess pieces rather than online (I’m too ashamed to share my ELO or Chess.com handle). However, that’s not the only reason why I’ve been seeking in-person opportunities for chess play. Adult life can get pretty lonely, and I think that even though Sardor and I have each other for company (wonderful company!), it’s different to have a group of people to regularly meet up with. Below are a few entries about my search for other chess players:
April 8, 2025: Monday Coffee Co. Open Play
I had joked about the irony and potential confusion about hosting an event that ran every Tuesday, at a place called Monday Coffee Company, but when we arrived, I did doubt for a second that we were in the right place. In fact, we were the only ones there besides the barista. To pass the time until the start of the event, we ordered some morning poison to start our day; Sardor got his usual, a large drip coffee served hot, and I decided to get adventurous with one of their specialty drinks called a Matcha Sunrise (iced matcha with aloe juice). As we sat waiting for our orders, enjoying the industrial, slightly brutalist design of the café, we heard the chime of the door opening, and three others trickled in discussing . A-ha. We had found our new crew!
Rudy was first to introduce herself. She’s a roulette dealer at a casino near O’Hare Airport, and started playing chess because she wanted to be able to beat her future grandchildren at something. Extremely valid reason, in my opinion. Paris was a young gentleman who seemed to know Rudy already; he had no idea how to play chess, and was here to learn for the first time. Peza (I’m not sure if I’m spelling that correctly) was a silver fox who had a master’s degree from UChicago in religious studies. He mentioned that he earned his degree in 2000. That’s the year I was born, I respond, and he leans back in his chair, eyes squinted in disbelieving laughter.
Julia and John came in with the boards and pieces. Two gorgeous, glamorous individuals. They recognized us from their first event at the California Clipper(!) and said they were glad to see us showing up today. John and I chatted for a bit about the current ongoing chess tournaments, and how ridiculous it was that Chess.com seemed to lean towards advertising the Freestyle Grand Slam over the literal Women’s World Championship. Just goes to show you what the chess world thinks of their women.

I played my first two games against Peza. He is much, much, stronger than me, but was gracious enough to let me try my hand at vengeance and play out dead lost positions against him. In these lost positions, he framed certain positions as puzzles, letting me work out certain positions. Man. If I were a kid again and could have had a chess teacher with Peza’s patience, I’d look forward to every class. I’d probably be master-level strength by now. Does it say something about me as a chess learner, if I say it’s satisfying for a game to end up in checkmate, even if I’m the loser?
I played my third game against someone named Dennis, and I lost. Dennis had shown up later in the event, in a very unique vintage Carhartt jacket he had thrifted in New York City. We both live along the same street, about eleven blocks apart. I don’t recall the game well, but I was playing as black, and I think we were quite evenly matched for the most part. I remember he had a pawn on e5 that was really irritating, and I spent too many moves trying to wipe it off the board with my bishop and knight. I remember trying to save my queen from his knight to no avail in the middle game, but we ended up trading off our queens anyway.
“What would Magnus do in this position?” I wondered aloud, earning a chuckle from my opponent. “Well… I doubt Magnus would be in either of our positions”, said Dennis, earning laughs from the whole table. I definitely blundered some pieces in the endgame. It took him a really long time to get me in a checkmate (we must have gone through a series of about 20 disjointed checks), but finally he got me in a mate after I lost my final rook. He was very friendly and upbeat, and was happy to chat after our game. I looked him up later, and it turns out he’s a very successful photographer, with about 60k followers on Instagram. Maybe I’ll see him at the next California Clipper event, and have my chance to exact vengeance.
April 10, 2025: “Not a Chess Club”
Sardor and I discovered this flyer at Music Box Theatre after watching a strange film about baseball called Eephus. I messaged the Instagram account on the flyer about this… private affair, and received an address to an apartment in Ukrainian Village. There was a deli in the neighborhood that Sardor had been interested in visiting, so we decided to stop by before heading to the chess meetup. After buying some mustard and horseradish from Ann’s Bakery and Deli, we entered a very strange apartment building, unlike anything I had ever seen on the South Side. Rather than enter straight from the sidewalk, we had to climb a wooden outdoor staircase leading to the front door. After we came inside, we struggled to find the correct door, which the owner of the anonymous Instagram had neglected to indicate in their message. We hovered awkwardly in the hallway, trying to listen for some kind of laughter or discussion, until another guest came in.
“Are you here for the chess thing–” I began to ask, and like magic, the correct door swung open; I guess the clubgoers must have heard us muttering in the hallway. We stumbled into a very cozy apartment, with several people already engrossed in gameplay or conversation, There was quite the cast present, and I didn’t get to know anyone super closely that night, so I’ll keep it simple: Shiying is generous. Junko is artsy. Kosi is elegant. Mitchell is mustached. Kolin is talkative. Moshe is distinguished. Jeare is soft-spoken. Amanda is composed. Carson is witty. Kendrick is busy. Qualifiers to follow at the next event.
I played my first game against Kolin, and I won. I was lucky to nab a queen in the beginning and outplayed him from that point. He kept talking about the songs he was writing for his musical and the strange people he met in the Nashville music industry, and it started to get a little irritating because he would take forever to move on his turn while talking, but soon enough, we played the endgame and I found a way to checkmate him. Besides the talking, he seems nice enough. He has an interesting mullet haircut, and seems like the kind of guy who would have thrived in one of the Chicagoland School of Rock music education programs playing bass or something.
I played my second game against Jeare, and I won. The game itself was drawn out and not very interesting, in my opinion, until the end, when I capitalized on a series of hanging pieces and wound up with a mate in 3. Something interesting happened, where I had Jeare’s king in check on the a-file, with a queen supplemented by a rook behind it. However, Jeare could get out of check by blocking with their bishop on a3 and counterchecking(!) my king on c1. Even with this interesting move, I believe it was still mate in three or four. We shook hands and went out to the patio, where everyone else had migrated.
I played my third game against someone named Moshe, and I lost. He spent most of the time chatting with Sardor in Russian, in an effort to improve his mother tongue (literally, his mom speaks Russian). Turns out he had even spent some time in Kazakhstan focused strictly on Russian study. We discussed some openings, and when he mentioned the Bongcloud, I decided to convince him to show him a different stupid opening called the Headache. Even after I made him play it, I lost! We then started playing new variations of chess, such as Queen vs Pawns (in which the pawns should have slight advantage if played perfectly) and Two-step King (in one person plays with a standard chess setup, and the other plays with only their king, except their king can move twice in one turn, and in and out of check). I hadn’t realized that the king would be so powerful with two moves instead of one.
All in all, a good night! Sardor enjoyed it much more than the California Clipper, and we hope to be back for their next meetup. Keep an eye out for the next installation of my chess journey!