I'm playing the Witcher 3 Blood and Wine expansion. There's a somewhat lengthy side-quest involving a tournament. However, the tournament isn't really the quest, it's just a means to an end, which is removing a curse from a young noble woman conducting the event. So to complete the quest, you don't have to win the tournmanet, just participate. But winning is sort of hard wired into us, gamers, right? There's some cool items to win, a big fight with a champion at the end... I easily won the first part (archery), but the second part (race) gave me some trouble. I had to try it a few times before I got the handle on it.

But the funny thing is - I kinda felt bad about retrying it and winning. It felt... false. I thought to my self "Geralt wouldn't really win this. It has nothing to do with what witchers do and these other knights train for these kind of tournaments all the time. I should have rolled with the first result, the one that was "real" for me. So when the last part came, the mock-battle, I gave it a good shot, but when I lost (fighting multiple opponents kinda sucks in this game, and I decided to play fair and use no signs or potions for this), I didn't try again. I rolled with the loss, and follwed what the quest really was about, the curse. And I felt oddly good with that. Losing actually felt like it added depth to the story.

What I'm leading to is - did that ever happen to you? Any other games out there were you could actually lose (I don't mean the protagonist being defeated in a cut-scene, I mean you the player losing and accepting that), but keep going, and where losing felt more right than winning?

Nice topic premise. Unfortunately there is very little representation on GOG other than the (excellent) Mutant League Football, but how about a sports game with a season/franchise mode?. I generally play them out and if I lose, I lose, but the season still continues to the end.

For "perfectionist" type one-death runs of games, almost anything would apply. It somehow feels the most "right" in fighting games to me. If I'm playing the Arcade mode and I lose, I feel there can be a certain type of fun in not continuing but rather starting back from the beginning.

I recently played "A legionary's life" which is about being a Roman legionary during the 2nd Punic war, with turn-based combat. You shouldn't exactly lose in battles, since the game's got permadeath, so a single loss will end your run. And killing enemies in combat is important for getting promotions and decorations. But your main goal is survival. Many of the battles are multi-stage, with each stage lasting only a set amount of time, before your line rotates to the back, allowing you some rest. So it's perfectly viable, and often necessary, to play it safe, be defensive and just wait for the end of the current battle stage...which definitely goes against the "You have to win every combat" mindset and imo adds some interesting realism to the game.

I have ethical debates save-spamming and even looking up cheats online let alone accepting "fate" within a game-world's story... and I certainly have existential dilemmas playing evil and morally ambiguous characters (yeah, my wife thinks I'm a "Boy Scout" to the extreme). There's no right or wrong -- it is a video game after all -- but accepting "fate" after a fair contest would seem to show that a player values fairness (although this could be debated), a good trait for a competitor... and Geralt is a perfect character for ethical questions on fairness.

I can think of one event in the game Final Fantasy 9, and it turns out that, to get the most useful reward, you need to not be the winner. After the event, the winner will get the item that she choose, and she joins your party just afterwords, and her item of choice is better than either of the other items you could have chosen.

Also, there are some games where deathwarping is a valid strategy. Basically, the idea is that, in some games, you respawn in a specific spot when you die, and sometimes that spot is closer to where you need to go, so to get there quickly, you die. An example would be Ultima 4, where death takes you back to Lord British, but with the loss of all unequipped items and with Gold and Food set to 200; given that there are orbs in the dungeon that permanently boost your stats at the cost of severe hit point damage to the character, this can be quite handy for boosting your stats. Or there's the Dragon Quest series, where a party wipe means you lose half your gold and are sent back to the last place you saved (and you can only save at kings (in DQ1-3) or churches (rest of the series); in the manipulated DQ1 speedrun rout, there are a few times when the RNG is manipulated to force an intentional death.

(Interestingly enough, in Ultims 6 and 7 there's a spell that acts like a deathwarp; that spell is first level (U6) or zeroth level (U7) and doesn't require reagents in either game. I guess Richard Gariott got tired of having people die intentionally and just gave up.)

I just remembered another good example: In Ultima 3 the game autosaves when somebody dies. This may sound bad, but this works in places you can't save, and can be used to smuggle a ship oustide of Lord British's castle, which is very handy in the DOS version where ships are scarce.

Now for something different, Celeste has one rather encouraging message, which the game gives you in a postcard at the start of (IIRC) Chapter 2: Be proud of your Death Count! The more you die, the more you're learning! Keep going! I just remembered another interesting case: There are cases in Final Fantasy 4 and 5 where you end up in a plot battle that is scripted to end on its own, but if you manage to party wipe during the battle, the game will keep going, so the death saves time. (In the FF5 case, it's not obvious that you can die in that fight because you don't die at 0 HP in that particular battle, but if you find a way to die other than damage, you can skip that scripted fight.)

Of course, I am reminded of another strange case: In Lufia 2, if you reach the end of the Ancient Cave, then lose to the boss, it counts as completing the dungeon. With that said, this boss heals you in the first round, never harms the party, and will leave in the fourth round, which (if that happens) does not count as completing the dungeon. (Unfortunately, in the boss's appearance in Lufia: The Legend Returns, a party wipe during that fight is still a game over, even though the fight is otherwise the same.) I don't know how the resource situation works for signs, but in general it's a bad idea to use potions in fights you're meant to lose (unless you're actually trying to win them, which is only sometimes possible), as you'll lose the potions and not have them for later use.

(This actually does become an issue in games with fights that you are supposed to lose, but where it is not obvoius that you're supposed to lose them.)

Just thought of another thing: In Rogue Legacy, you can't get stronger unless you die. If you never die, you'll be stuck with the starting character with starting stats the whole game.

Edit: Why the low rating for all this?

Closest I can think of is the original XCom. I naturally settled into a habit of loading a save each time things went bad. What made me stop wasn't so much that it didn't feel right, but that it wasn't fun anymore, because there was no risk at all. I might've then realized that that eats away at the authenticity of the game as well. By playing semi-ironman I got a game that was more fun, and felt more real.
Only 'semi' though, since the required concentration and arguably lottery style deaths/squad-wipes you sometimes experience made it difficult not to ever load a save.

I adopted the same approach with Xenonauts, where I hoped that I could finish the final fight with most, or at least most of my favorite soldiers alive. As it happened all my favorites died (my most favorite also poetically in the most heroic fashion), and only a single rookie managed to make it back to Earth. If I instead reloaded saves over and over again I don't think it would've been nearly as memorable experience as it was. As it stands it's a gaming memory that I'll probably remember for a very long time:
https://www.gog.com/forum/general/games_finished_in_2019/post979

Not exactly what you describe, but I have played games, where several outcomes (win-states) were possible, and where I went with a lesser good outcome, instead of retrying a passage in game over and over again.
As long as the outcome that I am able to achieve is acceptable for me, I don't need to try to get the "best" result to game on.

Winning and/or loosing are just means towards enjoyment. Regardless of any gamestate and any "ethical" conflicts individuals may or may not experience its palpable that anyone is able to enjoy any sort of game. I go so far and say that even discussions about "metaaspects" such as these profit towards the general enjoyment regarding any game. Personally, I feel that every game that doesn't have failure states do feel wrong. What matters is not to become too frustrated should one "not win".

I don't want to go into utilitarianism but thats just my perspective. I do not believe that there is no right way to play any game in the same vain as there is no right way to either win or lose and how to percieve these aspects of the game. As this thread already implies, some ways to win can feel like losing. Similarly, some lost parts of any game also can feel like you've actually had success.

As a hard-hitting example, lets pick a extreme game such as the X series. If you die in a game such as this you lose for good, you either have to reload a previous save or start anew. As a normal game can go as long as 2000 hours, dying can feel very frustrating but it doesn't have to be. These 2000 hours also include the learning experience itself regardless whether or not you've experienced success or failure. A lot of people never "finish" a game of X, simply because the path towards success was fun enough without experiencing a true "win".

All of these viewpoints are as individual as there are games.

I pretty much try to "roll with the punches and carry on" in most games I play that really let you -- even when the story is not serious or minimal/nonexistent. I leave save reloading for circumstances where I, the player, fucked up (e.g., by right-clicking when I meant to left-click, thereby attacking -- and angering or killing -- a neutral NPC instead of initiating a conversation with them). Even then, if the consequences of my mechanical fuck-up aren't too negative, I often won't bother if it would mean replaying the last half hour or more since I last saved.
EDIT: One real example of this is from The Witcher. Even though it was already getting to be an older game when I got it nearly six years ago, and my laptop (new at the time) is years newer than it and met all the minimum and most or all the recommended specs, I still had at least a couple parts where it chugged, the framerate dropped into probably the low double digits, and I consequently had a bad time trying to control Geralt and get much done. One such case (though not the worst) was when I tried to escort the barmaid home at night from the walled compound housing the inn/tavern/[whatever] where she worked. The glowing hounds showed up, but they brought a bunch of slowdown with them, and while I fruitlessly flailed away at some of the dogs (remember, that first game has timing-based melee combat -- not great when the game's lagging), she was off on her own trying to defend herself with a knife, and got killed before I could do much. I didn't really feel like replaying that whole bit -- especially given that there was no guarantee the same thing wouldn't happen again -- and I didn't figure there would be any major consequences to her death (i.e., being unable to finish the game), so I just let the failure stand, despite it not really being due to any choice I made or any gameplay challenge I failed fair and square.

There's a three-paragraph-long section in the introduction of Daggerfall's "User's Guide" that really expresses my position on this sort of thing. I don't feel like transcribing it all from the old, image-based PDF I have of the manual, so an attached screenshot will have to suffice. :P
EDIT: Obviously, since I invoked the name of Daggerfall, I should have also mentioned another case where I have no problem reloading saves: bugs. If the game seems to be kind of fucked, and I might be able to un-fuck it by loading an older save, I will have no compunctions about doing so.

Battletech is the first that comes to mind. I never reload. Even when I lose my best Mechs and pilots. Winning every fight would be real boring.

They SO should've had this option for the original Fable. During the Arena tournament quest when you fight against Whisper, you should be able to throw the fight with her, and let her win, so her brother Thunder would be cool and start to warm up to you. Instead for the rest of the game, he just has to put up with you.

EDIT: And you have to put up with him as well.

Actually, I remember a part in Dragon Quest 6, early in the game, where there's a competition to see who can solve a quest in a tower first. If you win, you get into the army, but if you lose, the guy who wins gets into the army instead. In any case, that other guy will join your party either way, and after an event whoever didn't get into the army before gets in now.

DQ6 also has another event later on, where you have to go into the dungeon and will get a special weapon if you kill the boss. However, you get beaten to the boss (no branching paths here, it always happens), and so you don't get that weapon. The character in question eventually joins your party, but not until much later in the game (but he still has the weapon he got), and there's a way to get that boss in your party as well.

I do this on Fire Pro Wrestling a lot. Putting on the highest rated match is the main thing in that game, and a lot of times the best match result is you losing a well-fought match. Especially in the campaign modes where you're playing a rookie coming out of training. No one just comes in and wins everything all the time. Fans turn on over-pushed wrestlers quickly.

X-Com style games are great for that kind of emergent moments. I think I like it even more in Massive Chalice, because of the whole system of having your heroes age and possibly have families together, children that will replace them, or taking on other non-combat duties. It makes them feel a bit more "real", and having an aging hero do this kind of last hurrah after a long career is all the more satisfying.