Another great thread. Thanks to the OP and all follow-up posts.
I am trying to remember with 100% certainty which was my first, but I am only sure it was one of two events that were approximately in the same timeframe. Like several others here, I had previously only played casual players, and the (seemingly ubiquitous) “teacher that nobody could beat”, who I had somehow managed to beat. I’d learn quickly that I’d really had no measure of my true skill (none of these people had ever been to a USCF event), but with an inflated degree of confidence I started reading about USCF events and looking for a few to enter.
It was 1974 and I was a high school junior in a small/mid-sized parochial school in Southwest CT (Fairfield Cty). As such I lived very much on the NYC commuter line, just a few miles away from the NY state line, and literally a stone’s throw (for a decent outfielder) from both I95 and the commuter train station. So I knew where these places in the tournament ads were (both NYC and Westchester Cty, primarily), and I knew it would be easy to get to them.
The one event that I think was first for me (if not, assuredly second) was in a fairly upscale hotel in Westchester - I think Scarsdale, if not Rye or White Plains. (This is a bit of a blur at this point! But that detail is unimportant.) This was a two-day, five-round SS event - all high school players. I think there were about 50-70 kids in it. I had no idea what “SS” meant, but quickly learned that as my performance went up, so would the degree of difficulty - and also the converse.
My HS teacher took me to this, both days, which was a significant sacrifice of time on his part for an activity that I later realized was only a casual interest for him. He was a semi-retired PhD who had actually been in the national spotlight a few years earlier, and was fairly well-known around the area - something he didn’t seek for himself, but was put upon him by very significant events beyond his control. I will choose not to elaborate here out of deference to his family (he is gone now). But my point is that he was a teacher that I respected greatly, and out of his kindness he spent a very full weekend with me at this tournament, recognizing that it was more than a casual interest for me at the time.
The other event (probably around that Christmas break) was possibly one that was mentioned (or at least the same type) by an earlier poster - a huge event at the Hotel McAlpin, about an eight-block walk from Grand Central. This one had a couple hundred high schoolers, and I vividly remember seeing the name “Michael Rohde” at the very top of the board - with a rating at that time somewhere around 2000-2100. It might as well have said “infinity”, for most of us - I was never paired with him, but enjoyed seeing who he was and watching a few minutes of his play (when my own game was over). I knew it was a name that would become well-known around the USCF, which of course was the case.
From these, four of my own misconceptions come to mind - each recalled with a touch of humor for me, now:
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I had no idea how to dress for these events, but decided I’d err on the safe side. Influenced perhaps by my parochial school culture, I donned a sportsjacket and tie! I quickly realized that seeing a hs chess player in a tie (which I actually hated myself) was identically as rare as seeing a female player in those days - there was exactly one, of each of us! Remarkably I kept it on - probably not wanting to consciously admit my miscalculation - until one kid (who I’d never met) just came up to me and said, “Excuse me - but can you tell me why you’re dressed up like that?” We both just laughed, and I said, “No, actually, I can’t”… and the tie came off (for good).
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My parents had bought me a BEAUTIFUL set for Christmas, which was an inlaid wood board/box, and a hand-carved wooden set - with 6"(!) Kings. I brought that to the tournament, of course… quite proudly! But my first opponent balked, saying I couldn’t use a non-standard set. (My teacher had no clue if that was right.) I asked the TD, and of course with the oversized pieces he told me that my opponent was right. I was heartbroken and didn’t want to tell my mother, but I eventually did. Within a short time I came to not only understand the objection, but actually agree with it - it is just ‘different’ to look at the game on that set (with an otherwise regular-sized board), and so I never brought it to tournaments again. But I otherwise love that set, and I STILL have it (which my mother enjoys, 35+ years later now). It is set up in my living room and used, often, for casual games with friends and my kids.
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I had previously had no idea about the typical practices or “conventions” regarding resigning a game. In fact I wasn’t even familiar with the concept - having not lost very many games prior to my first USCF entry. I remember playing in an extremely lost position - probably down two pieces AND a couple pawns - and playing it out to the bitter end, thinking that somehow my opponent would blunder into some ridiculously trivial stalemate, or the like. I remember one opponent getting frustrated with me for that! Of course the maxim that ‘no one has ever won by resigning’ has validity, but on at least that occasion (and maybe twice) I had essentially 0% chance of even a draw, and SHOULD have resigned. However on this point I’ve now had a lot of experience, and am adept at resigning - quite competently!

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Finally, and again like quite a few other posters here, my non-quantitative, non-realistic, preconceived opinion of my own playing skill was quickly proved to be quite inflated. I actually went into this tournament hoping I could win a prize, but quickly got pummelled in my very first game. I am grasping for precision in my memory here, but I’m certain I was not better than 2.0 (of 5) in that first event - I think, probably, it was 1.5. Of course, that result buried me in the pack of also-rans. Amazingly to me at the time, I clearly recall my teacher being totally fine, not at all upset (or probably surprised) with this result, which by contrast had me a bit upset. After my second loss he counseled me with a golf analogy (I wasn’t a golfer, but he was - and was also the hs golf coach): “When a good golfer blows a hole, he knows he has to simply put it behind him, and move on to the next hole”…which of course was a VERY good analogy, and sound advice. All in all he was quite encouraging to me. But my first rating was indeed unimpressive: somewhere around 1100. Before I finished HS it had “peaked” (all relative!) around 1600, then later sagged back to the high 1400s. But I was always looking up at elites like the "Michael Rohde"s of the USCF; of course, we were all still looking up, WAY up, at the World Champ, RJF-2810!