A friend/coworker of mine and his wife hosted a weekly boardgame night that I attended. Most of the other guests were kinda flaky, and this one particular day, I was the only one who showed up. So it was just me, my friend, and his wife.
Someone suggested Dixit, which I had never played before, but it sounded fun and I was down to play. So we broke it out, shuffled, and started the game.
Now, if you don't know how Dixit works, it's basically a deck of cards with pictures on them. One of a toy abacus. Another of a child pointing a toy sword at a dragon. Another of a winding staircase with a snail at the bottom. Etc.
In one version of the game similar to Apples to Apples or Scategories, everyone gets a hand of cards which they keep hidden. The dealer announces a clue and everyone (including the dealer) contributes a card from their hands face-down to the center of the table and the dealer shuffles them together and reveals them all at once without revealing whose card is whose. Then players vote which one they think matches the clue. You get points as a player if others vote for your card or if you vote for the one the dealer picked. As a dealer, you get points if close to 50% of the players vote for yours.
I was the dealer this round. One of the cards in my hand was of a ship's anchor. That's when it came to me.
See, the friend/coworker and I both worked in web software development. His wife didn't. And I came up with the perfect play. I gave the clue "hyperlink." Hyperlinks on web pages are created using the HTML <a> tag. The "a" stands for "anchor." And any web developer would know that.
When the vote came in, I got one vote for my card from my friend and his wife failed to select the correct card and so didn't get any points. It was a slam dunk move. But I felt a little bad for excluding my friend's wife from an inside-knowledge thing.
The next round, my friend was the dealer and he picked a rule/card that was an inside-knowledge thing between the two of them. (A line from a poem they both knew well, the next line of which related to the picture of the card.) So I was glad of that.
I play an ongoing ladder/tournament for a Scrabble clone (Wordfeud). I'm kinda stuck at a middling level because of certain holes in my game that I refuse to fix because it would be boring (e.g. I could know what your last 7 tiles are but I do not intend to figure it out), but I'm decent. One of the ways I power through the lower tiers was by realizing that you can play defensively, specifically by shoving 'C' and 'V' in places that fuck up your opponent's access to high-scoring tiles (because they have no two-letter words to jump off from), or just leaving points on the rack because maximizing each turn would open things up on the board.
New players simply cannot handle this. I'm sure they don't have much fun, but I win and go back up to the levels where the strategy helps some but you can't rely on it. Higher level players can bust through by sheer force of pattern recognition and vocabulary, or they can build words that open up so many avenues that they can withstand my getting some points too, or them fuckers DO keep track of which tiles are left (the gall!). I'm trying to remember that I'm good enough that an open board can help me too, but my tendencies are still pretty defensive.
Back when Words With Friends was big, I developed a reputation among my friend groups for being very good. I wasn't terribly good, but I noticed there was no penalty for misspelling a word. So each turn, I'd try a bunch of high-scoring combinations that seemed like they might be words, and eventually one would work.
It's sort of inherent to scrabble-like apps, where there's so many ways you could mess something up. I am not above taking a flyer on things, but I try not to do it any more than I assume my opponents would. Anyway, having played a lot by now, I know most of the common and medium-weird words, so there's not a lot for me to guess at, and I'm only rarely surprised when something an opponent plays is a word.