What better place to start than the king of games, what most folks think you're talking about when you say you're playing a "serious" game.
Chess has, I think, been corrupted by its own success.
Back in High School I used to try and play Chess. I'd go by the Chess club at lunch because that's what all the nerds did. But after a year or so I gave up the habit, because I never found Chess that enjoyable--it had too wide of a decision tree, and thus required too much thought--and because I decided that the Chess club members were even more socially retarded than I. That's simply a statement that I really have tried Chess, however, not a statement of why I don't like it.
The biggest actual problem with Chess is the huge amount of literature that has been written about it: the exhaustive listings of starting moves, strategems, and counter-strategems. The necessity to have memorized these hundreds or thousands of standard strategies turns Chess into a game of memory rather than strategy.
That we can now program computers to play as well as the top humans says a lot about how staid and automatic this game has become at any truly competitive level.
Scrabble has much the same problem. It can be perfectly enjoyable at a non-competitive level where players drop down words with their spouses, friends, or loved ones, and might know that "aa" and "qat" are perfectly acceptable words, but not a lot more.
Where Scrabble falls apart, however, is again at the competitive level. It was Word Freak which showed me how truly degenerate Scrabble play is among professionals, with its descriptions of obsessive and continuous memorization of 3-, 4-, and even 5-letter words. Like Chess, Scrabble loses its strategy at higher levels of play and instead becomes a game of memory.
Bridge is a fine, though not particularly notable, trick-taking game. The bidding system for Bridge is what really stinks.
I played Bridge for a while when courting my then wife-to-be, and in the process I studied crib sheets carefully. I learned what bids to make with how many points and started to eke out the meanings of what my partner might mean when she was making a bid herself.
I eventually came to the realization that there was no real game to the bidding of Bridge, it was simply the act of learning a secret code--a foreign language--and then applying that linguistic knowledge. And I decided that if I wanted a foreign language in my gaming I'd do better to work on a more useful one, for example by playing A Game of Thrones entirely in Spanish:
"You deseo ... uh ... ser un amigo con blanco. Lobos blancos? Blanco y verde solamente amigos. Muerto ... muertamos rojo. Uh ... Rojo no juega. El pollo rojo esta en la casa loca, mis amigos."
Texas Hold 'em
Before I got involved in European games, I used to have a Poker night every week. It was always Dealer's Choice play, and inevitably someone would offer up one of the Texas Hold 'em variants to play. Usually these games just confounded me, because I didn't understand where the game was.
More recently I was given a review copy of a Texas Hold 'em computer game, and I've now spent several hours trying it out. And I've come to the conclusion that this is scarcely a game worth playing.
Clearly Texas Hold 'em is intended to be a game of almost pure bluff. You're given two cards, and then you can combine those with a set of (eventually) five face-up cards to form the best five-card hand you can. You never get to see anyone else's cards until the very end, and so you have to make your assessment of other peoples' strengths solely based on their bids (and their past behavior).
However, as a game of pure bluff, this is one of the more boring that I've seen. In a 10-player game, you can usually expect 6-9 players to fold before any cards are flipped face-up. The vast majority of games end with the penultimate person folding. For the most part, you don't want to stay in unless you have a pocket pair or a nice high matched set in your hidden cards. So round after round after round it's nothing but "fold", "fold", "fold", "call", "fold", "fold". I think it speaks a lot for how broken this game is that in most games two players are forced to bid--else the folding which takes up the vast majority of gameplay would take up just about all of it.
The forced bids (which increase in value throughout the game) also seem to largely break endgame play where the last few players have to bid every round and the amounts are so high that victory swings back and forth based largely on the draw of the cards.
The problem with Texas Hold 'em is, pretty clearly, that it was developed for TV play. The one "exciting" part of the game is when a couple of players are "all in" and then you slowly reveal the common cards one at a time to see who the actual winner is. Of course, this is a probabilistically random event, with no strategy at all because you've already made your bidding decisions.
On TV these showdowns can look great, and conversely you don't have to sit through hours of people folding. In real life you do, marking Texas Hold 'em as a failure in my book despite its immense popularity.
At last we come to one of These Games of Ours. To be honest, I do like Puerto Rico. I think it's an entirely clever and fun game and I often enjoy playing it with some of my best friends.
What I don't like, however, is many of the people who play Puerto Rico. As Puerto Rico has gained renown as one of the most strategic and thoughtful games of the German Invasion, it's begun to suffer from Chess Syndrome, with pre-programmed moves and "optimal" strategies slowly sucking the life out of the game.
Take a moment and listen to the conversation at one of the nearby Puerto Rico tables:
"Well, I would have won if I hadn't been sitting to Jeremy's right, and he kept taking Producer when there was no logical reason for him to do so."
"So I took Producer which of course meant that Jamie Sold, then Alexa shipped, which was exactly what I expected because it then let me build on the next turn, though that played into Alexa's hands who had saved up a larger store of money, but if I'd instead built with my then lesser resources, then Jamie would have produced, I would have gotten left with no coffee and Alexa would have shipped anyway, and shipping wasn't an option for me either because then Jamie would still have sold and Alexa would have refused to produce at all ..."
"No, no, if he took builder then you have to grab a quarry with settler. Anything else is a subpar move."
There's nothing like a bit of I-know-better-than-you-itis to destroy the fun factor of a game.
(Jeremy Avery expanded on this same topic a while ago in The Jedi of Puerto Rico, though I only found that article after I drafted the above. Ironically my use of the name "Jeremy" in one of my examples had nothing to do with his scribing.)
Perhaps listing this as five games I don't like was a bit strong. I actually like Scrabble and Puerto Rico, two of the games on the list, and if I didn't find it as boring as staring at a blank wall, I'd think the gameplay of Chess was OK.
However each of the five games I list this week, from Chess to Puerto Rico, has what I'd call meta-problems: issues outside the central focus of the game which can still destroy any fun that the game can offer.
Published moves, rote memorization of words, secret codes, made for TV play, and obnoxious know-it-alls, while somewhat beyond the internal scope of these games, still can contribute to their fun (or lack thereof) in the real world.