I’m planning my next session, and I want to have a moment where my players do something bad, and was wondering how I can make them feel genuinely regretful/guilty. Any suggestions on how I can achieve this?
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“Libraries were full of ideas—perhaps the most dangerous and powerful of all weapons.”
In the campaign I am currently deeming, I had a situation that I think might apply. One of the PCs (and his player) genuinely thought that by killing the young girl NPC that it would end the nightmare because they thought she was the BBE. She wasn’t, she was sposta be there to help them when they got stuck. See, she was psychic and had visions of people dying. They thought she was behind the green curtain so he bashed her face in (repeatedly) with a coal shovel. When that didn’t end the nightmare they eventually (big shocker this) tracked the gorram clues and realized there was an extradimensional creature behind the nightmare and they eventually defeated it and everyone woke up….
Next thing they knew there’s a shrieking wail of despair from downstairs and they all run to discover the little girls mother wailing over the corpse of her daughter whose face had apparently been chopped up with a blunt object. (He used the edge of the shovel.) The PC’s squire (who was sweet on the girl as they were both around 14ish) was throwing up in the corner. One of his other retainers (who had been knocking boots with the mom) was ghastly white, a sight on a grizzled veteran. The third retainer (the PC has the Knight Background) spent the next two days inside a bottle….
And, because she was a Psychic she is now haunting that PC. Every once in a while he gets a flash of the girl in his mind (because I text them to the player). The whole party of both players and PCs were guilty for weeks, so guilty in fact that they haven’t arbitrarily resort to violence since and it’s been about 6 months.
Absolutely agree with the sentiment that the actions need to wholly belong to the players.
To assist in achieving the feeling of guilt, it usually will require a tough moral choice, some ambiguity in the environment that can be cleared through learning and social interaction and the discovery of wrong doing that holds emotional or ethical consequence. The answers and truth should be readily available to those that seek it, but not obvious at first glance.
I have a PC that is being visited by a Night Hag in the night, and is leaving images of the PC grinning and smiling as he kills his foes while he dreams. The party sought out the hag by following a lead into the sewers to find a twisted creature that resembled the hag and an abomination. The party initiated combat, with psychic phrases entering the party's thoughts to the effect of don't let them kill us, you're making us hurt, she's gonna claim us. At the very end of the fight, the player whose PC is being visited held off one of their attacks and finally asked a question of their foe: who's trying to claim you? The response was the name of the hag. Then the creature succumbed to their trauma and reverted to their true form. The wretch and abomination were dispatched and as the bodies dissolved the party members were introduced to a brother and sister the hag had twisted into these creatures. Restored in death to what had been taken from them in life.
The party is much more willing to attempt a diplomatic resolution now. At least until they find this hag, then I don't believe conversation will be on the table. They've grown to absolutely despise hags.
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“Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one's lifetime.” - Mark Twain - Innocents Abroad
Give them something awful and let temptation do it’s thing.
In one game I gave the players a book with an ice devil bound to it. The mechanics made it next to impossible to use it for combat (1 hour ritual to cast, had to draw up a contract governing what it was, wasn’t allowed to do while it was “out” of the book, etc) and then just let nature take its course. Sure enough, they got frustrated having a hard time finding evidence against a noble they thought was evil (he wasn’t ) so they released the ice devil with painfully explicit instructions on how to go around the town doing terrible things and framing the noble for it. By the time it was over, hundreds of people were dead and much of the noble district of the town was in ruins. And then they got word the noble they had been trying to frame had just been killed fighting some of the real BBEG forces.
One PC was so overcome with guilt the player had him wander off for a few months to clear his head while he rolled up a temporary replacement.
Rollback Post to RevisionRollBack
PC - Ethel - Human - Lvl 4 Necromancer - Undying Dragons * Serge Marshblade - Human - Lvl 5 Eldritch Knight - Hoard of the Dragon Queen
DM -(Homebrew) Heroes of Bardstown *Red Dead Annihilation: ToA *Where the Cold Winds Blow : DoIP * Covetous, Dragonish Thoughts: HotDQ * Red Wine, Black Rose: CoS * Greyhawk: Tides of War
Is anyone in the party a disciple of the Storm Lord? if so, have a bolt of lightning strike down whenever they do some epic maneuver/cast some awesome spell/etc. A few sessions in, reveal to the player that the Storm Lord has been nuking a kitten with each bolt of lightning they hear nearby as a way of augmenting the player's innate abilities.
On a more serious note, I'm concerned that your post states " I want to have a moment where my players do something bad". As some have already said, forcing a "bad" action on the party won't result in a strong emotional response, aside from maybe not loving the railroading effect (especially if they didn't want to do a bad thing to begin with).
The wikipedia entry on The Trolley Problem might be useful to you. TLDR: Give them a difficult choice that has no guiltless outcome, then have the world respond to the consequences of their decisions.
Not to quibble too much, but the players or the characters?
That’s not a quibble at all. That’s an important distinction far too often overlooked.
Yeah this is really important. The characters can feel bad: they players should not.
Do not just plan in something to make either players or characters feel bad. Don't presuppose reactions. You should ensure that it is the character's actions that lead to the badness, and choices they have made or it will feel awful for them.
Here's an example of one I did that worked, and one where I messed up:
Worked:
A character has carried around an evil book that teaches him bonus Battlemaster manoeuvres since level 1. The book contains the souls of those that have previously read it. It has gradually been consuming him for 8 levels. The PC befriends a child who, impressed with his swordsman skills wants to learn. The PC left his pack unattended, the child read the book and disappeared. The PCs (not knowing this) searched for the kid, but to no avail. They cast Locate Creature and it pointed to the book. The PC is now on a mission to destroy the book and save the child's soul. Why it works: The PC knew the book was evil, it was his actions that caused it, there was lots of foreshadowing and build up, and importantly - the PC can redeem himself.
Did not work:
A character (same campaign) took out a mid level boss, and gained his Black Mark. This magic item could not be removed, and would kill him in 30 days. He went to great lengths to conduct a ritual to remove the mark, but involved making a pact with a Great Old One. The GOO promised him it would be removed if he killed some of his old friends, which he did... but when it was over the mark left him and flew to the nearest person - a party member. The deal had only been "Do this and I will remove it for you" and I thought they'd see the duplicity as fun. It was intended as a "This is the price of making pacts with great evil," moment and it fit the narrative... but the player was upset because they felt awful for the other player, and that player was actually really annoyed. The session was ending there, and rather than "Oh god, now we have to find another way" there was a really bad atmosphere. For the next week I had to do some extra work. I asked both players involved what their characters would do. The character with the mark would try to retain it rather than let it go to his friend. The friend would try to take it from him (even if the player didn't like it). As a result, both tried to take it, the GOO would not continue his pact with the deal-maker, and blew up the heart of the character in vengeance. A surge of wild magic (the new recipient being a level 7 Wild Magic Barbarian/1 Wild Magic Sorcerer) created a new wild-magic heart for the Blood Hunter and everyone was happy with the result. The initial idea upset players - the resolution let them solve it through their own actions, and so resolved the situation.
TLDR: Don't force anything on the players, but let their actions have consequences (how often have we heard this haha).
The wikipedia entry on The Trolley Problem might be useful to you. TLDR: Give them a difficult choice that has no guiltless outcome, then have the world respond to the consequences of their decisions.
There may be some groups of players who would enjoy this dilemma, but personally I will never present this to the players.
D&D is a game, and there's an expectation that as players, you can win - or in other words, you can create desirable outcomes. If no outcome is desirable, then what is the point of the game? I have yet to encounter a game scenario where making "the least awful choice" leads to the players feeling satisfied unless they are able to come out of it thinking "this was definitely the right choice, and we were not responsible for lost NPC lives."
I don't think that guilt-laden outcomes should ever be forced on players, and there's always the chance that the players, objecting to being forced into an unwinnable scenario, choose not to care about them.
Since D&D is a fantasy adventure game, I think it's better to go in with a Kobayashi Maru mentality. Present them with an unwinnable scenario, and let them break all of the rules and expectations so that they get to win it.
The wikipedia entry on The Trolley Problem might be useful to you. TLDR: Give them a difficult choice that has no guiltless outcome, then have the world respond to the consequences of their decisions.
There may be some groups of players who would enjoy this dilemma, but personally I will never present this to the players.
D&D is a game, and there's an expectation that as players, you can win - or in other words, you can create desirable outcomes. If no outcome is desirable, then what is the point of the game? I have yet to encounter a game scenario where making "the least awful choice" leads to the players feeling satisfied unless they are able to come out of it thinking "this was definitely the right choice, and we were not responsible for lost NPC lives."
I don't think that guilt-laden outcomes should ever be forced on players, and there's always the chance that the players, objecting to being forced into an unwinnable scenario, choose not to care about them.
Since D&D is a fantasy adventure game, I think it's better to go in with a Kobayashi Maru mentality. Present them with an unwinnable scenario, and let them break all of the rules and expectations so that they get to win it.
This is party dependent, my games have always been darker and grittier and my players love that, I never present unwinnable situations but, I do present times when it is clear a decision must be made. One campaign I did put the players in a time loop, to get out one of the things that had to happen was a 10yo boy had to die. The players got to know that boy over the 2 1/2 years of playing time, they got to love his character, they re lived the same 48 hour period a total of 113 times and the last 22 was them trying to figure out how to end the loop and keep him alive. In the end they killed him (he was a vessel for a great evil, the loop was put in place by a powerful being to stop this evils emergence), and the other 2 NPCs that had to die as they where also vessels (a young adult and a much older adult). They then defeated the evil protected the 3 souls and saved them preventing it from rising.
I considered allowing them to save the boy but the whole point of the campaign was sacrifice and living in ignorance. Only the characters knew about the loop at the start of the campaign, they had a choice at the end, go back into the loop ignorant knowing it would continue forever this being trapped but an entire town trapped with it, or destroy it forever but at great cost.
In the post campaign wrap up the players told me they enjoyed the story I told and agree, had I let them “save” the boy then they would have felt cheapened or pandered to.
If the players deserve to feel bad for their actions then let them. There’s nothing wrong with a GM intentionally eliciting a desired emotional response from their players, we do it all the time. Every time they cheer when we wanted them to and we smile, we’ve just done it. There’s nothing even wrong with the emotional response being guilt if they have done something to feel guilty for. But the distinctions between PC (mechanics), character (RP), and player (RPer) is still very significant and far too often overlooked.
Put yourself in the mind of the monster. I had one player absolutely refuse to attack the goblin priest after he yelled at the players to stop killing their children, taking their treasure and food. Of course their food was human legs. There is a lot you can do when you play the empathy card by the bad guys.
Put yourself in the mind of the monster. I had one player absolutely refuse to attack the goblin priest after he yelled at the players to stop killing their children, taking their treasure and food. Of course their food was human legs. There is a lot you can do when you play the empathy card by the bad guys.
I've had a fair amount of success perplexing players when the bad guy does nothing but talk reasonably at them.
Also begs a think on your game settings culture. Are the consequences guilt (kinda on the player to generate in their PC) or shame/dishonor. The latter becomes an ambience burden the DM has more latitude and agency in imposing, but presumes a different moral foundation than a guilt driven character presumption. I remember the old Battletech fictions had lots of inspiration on how to contend with being a dishonored protagonist and the like.
Getting the players to role play "my god, what have I done?" is a lot harder to pull off in my opinion.
Rollback Post to RevisionRollBack
Jander Sunstar is the thinking person's Drizzt, fight me.
If the players deserve to feel bad for their actions then let them. There’s nothing wrong with a GM intentionally eliciting a desired emotional response from their players, we do it all the time. Every time they cheer when we wanted them to and we smile, we’ve just done it. There’s nothing even wrong with the emotional response being guilt if they have done something to feel guilty for. But the distinctions between PC (mechanics), character (RP), and player (RPer) is still very significant and far too often overlooked.
Characters shouldn't be made to feel guilty, that should be a choice for the player.
Guilt/regret is also something that is much harder to judge than whether both the players and characters will be happy if they beat the evil dragon. If you know your group well enough and are absolutely sure they'll be ok with it then that's a call that can be made, but it's much more likely to be wrong. Nearly every post that describes having done this in this thread revolves around the killing of a child (including my own, though the child isn't dead in mine and the player can still save the child). I know that my players would absolutely hate the other examples given.
Part of the reason guilty outcomes should not be forced is that either the player has to alter their character's personality to match the DM's design, or they have to decide they simply don't feel remorse (which again may be a change).
Personally I think that if you only offer "the lesser of two evils" then the PCs are being railroaded, there's just a branch in the track. Going Kobayashi Maru allows the players to do whatever they want, even if they fail. Not long ago I ran the siege of a monastery against 3 airships and an army. The PCs could choose to defend the gatehouse, the temple, the stairs to a dungeon, or the civilian area. Depending on which area they did first, events would be different in the other areas they then went to. There was a complex chart for the battle's progression depending on the order they assisted the defenders in (e.g. they don't defend the gate from giants in phase 1, so in phase 2 the giants control the gate, by phase 3 more enemies enter the gate), and there would only be time to go to 3 out of 4.
My players ignored everything I'd planned, cast Fly, flew up and attacked the flagship head on and took it out. This then caused ripples. I was totally surprised by it, and it's the best thing that's ever happened in my game.
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I’m planning my next session, and I want to have a moment where my players do something bad, and was wondering how I can make them feel genuinely regretful/guilty. Any suggestions on how I can achieve this?
“Libraries were full of ideas—perhaps the most dangerous and powerful of all weapons.”
To start with, it should be something they did on their own, not something they did because the DM manipulated them into doing it...
In the campaign I am currently deeming, I had a situation that I think might apply. One of the PCs (and his player) genuinely thought that by killing the young girl NPC that it would end the nightmare because they thought she was the BBE. She wasn’t, she was sposta be there to help them when they got stuck. See, she was psychic and had visions of people dying. They thought she was behind the green curtain so he bashed her face in (repeatedly) with a coal shovel. When that didn’t end the nightmare they eventually (big shocker this) tracked the gorram clues and realized there was an extradimensional creature behind the nightmare and they eventually defeated it and everyone woke up….
Next thing they knew there’s a shrieking wail of despair from downstairs and they all run to discover the little girls mother wailing over the corpse of her daughter whose face had apparently been chopped up with a blunt object. (He used the edge of the shovel.) The PC’s squire (who was sweet on the girl as they were both around 14ish) was throwing up in the corner. One of his other retainers (who had been knocking boots with the mom) was ghastly white, a sight on a grizzled veteran. The third retainer (the PC has the Knight Background) spent the next two days inside a bottle….
And, because she was a Psychic she is now haunting that PC. Every once in a while he gets a flash of the girl in his mind (because I text them to the player). The whole party of both players and PCs were guilty for weeks, so guilty in fact that they haven’t arbitrarily resort to violence since and it’s been about 6 months.
Does that help?
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Oh lord, yeah, that would do it.
Absolutely agree with the sentiment that the actions need to wholly belong to the players.
To assist in achieving the feeling of guilt, it usually will require a tough moral choice, some ambiguity in the environment that can be cleared through learning and social interaction and the discovery of wrong doing that holds emotional or ethical consequence. The answers and truth should be readily available to those that seek it, but not obvious at first glance.
I have a PC that is being visited by a Night Hag in the night, and is leaving images of the PC grinning and smiling as he kills his foes while he dreams. The party sought out the hag by following a lead into the sewers to find a twisted creature that resembled the hag and an abomination. The party initiated combat, with psychic phrases entering the party's thoughts to the effect of don't let them kill us, you're making us hurt, she's gonna claim us. At the very end of the fight, the player whose PC is being visited held off one of their attacks and finally asked a question of their foe: who's trying to claim you? The response was the name of the hag. Then the creature succumbed to their trauma and reverted to their true form. The wretch and abomination were dispatched and as the bodies dissolved the party members were introduced to a brother and sister the hag had twisted into these creatures. Restored in death to what had been taken from them in life.
The party is much more willing to attempt a diplomatic resolution now. At least until they find this hag, then I don't believe conversation will be on the table. They've grown to absolutely despise hags.
“Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one's lifetime.” - Mark Twain - Innocents Abroad
Regretful? I just tell them this campaign only uses standard array. :P
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Give them something awful and let temptation do it’s thing.
In one game I gave the players a book with an ice devil bound to it. The mechanics made it next to impossible to use it for combat (1 hour ritual to cast, had to draw up a contract governing what it was, wasn’t allowed to do while it was “out” of the book, etc) and then just let nature take its course. Sure enough, they got frustrated having a hard time finding evidence against a noble they thought was evil (he wasn’t ) so they released the ice devil with painfully explicit instructions on how to go around the town doing terrible things and framing the noble for it. By the time it was over, hundreds of people were dead and much of the noble district of the town was in ruins. And then they got word the noble they had been trying to frame had just been killed fighting some of the real BBEG forces.
One PC was so overcome with guilt the player had him wander off for a few months to clear his head while he rolled up a temporary replacement.
PC - Ethel - Human - Lvl 4 Necromancer - Undying Dragons * Serge Marshblade - Human - Lvl 5 Eldritch Knight - Hoard of the Dragon Queen
DM - (Homebrew) Heroes of Bardstown * Red Dead Annihilation: ToA * Where the Cold Winds Blow : DoIP * Covetous, Dragonish Thoughts: HotDQ * Red Wine, Black Rose: CoS * Greyhawk: Tides of War
Depends on what they do. If you punish them too much, they will feel railroaded.
If they commit a crime, send the town guard on them.
If they kill and NPC that didn’t deserve it, have the news get around and other NPCs that aren’t loyal to the party avoid them.
Don’t do anything OOC because as a player it is the most annoying thing ever to be punished OOC for something that a character did.
Is anyone in the party a disciple of the Storm Lord? if so, have a bolt of lightning strike down whenever they do some epic maneuver/cast some awesome spell/etc. A few sessions in, reveal to the player that the Storm Lord has been nuking a kitten with each bolt of lightning they hear nearby as a way of augmenting the player's innate abilities.
On a more serious note, I'm concerned that your post states " I want to have a moment where my players do something bad". As some have already said, forcing a "bad" action on the party won't result in a strong emotional response, aside from maybe not loving the railroading effect (especially if they didn't want to do a bad thing to begin with).
The wikipedia entry on The Trolley Problem might be useful to you. TLDR: Give them a difficult choice that has no guiltless outcome, then have the world respond to the consequences of their decisions.
Not to quibble too much, but the players or the characters?
That’s not a quibble at all. That’s an important distinction far too often overlooked.
Creating Epic Boons on DDB
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Yeah this is really important. The characters can feel bad: they players should not.
Do not just plan in something to make either players or characters feel bad. Don't presuppose reactions. You should ensure that it is the character's actions that lead to the badness, and choices they have made or it will feel awful for them.
Here's an example of one I did that worked, and one where I messed up:
Worked:
A character has carried around an evil book that teaches him bonus Battlemaster manoeuvres since level 1. The book contains the souls of those that have previously read it. It has gradually been consuming him for 8 levels. The PC befriends a child who, impressed with his swordsman skills wants to learn. The PC left his pack unattended, the child read the book and disappeared. The PCs (not knowing this) searched for the kid, but to no avail. They cast Locate Creature and it pointed to the book. The PC is now on a mission to destroy the book and save the child's soul. Why it works: The PC knew the book was evil, it was his actions that caused it, there was lots of foreshadowing and build up, and importantly - the PC can redeem himself.
Did not work:
A character (same campaign) took out a mid level boss, and gained his Black Mark. This magic item could not be removed, and would kill him in 30 days. He went to great lengths to conduct a ritual to remove the mark, but involved making a pact with a Great Old One. The GOO promised him it would be removed if he killed some of his old friends, which he did... but when it was over the mark left him and flew to the nearest person - a party member. The deal had only been "Do this and I will remove it for you" and I thought they'd see the duplicity as fun. It was intended as a "This is the price of making pacts with great evil," moment and it fit the narrative... but the player was upset because they felt awful for the other player, and that player was actually really annoyed. The session was ending there, and rather than "Oh god, now we have to find another way" there was a really bad atmosphere. For the next week I had to do some extra work. I asked both players involved what their characters would do. The character with the mark would try to retain it rather than let it go to his friend. The friend would try to take it from him (even if the player didn't like it). As a result, both tried to take it, the GOO would not continue his pact with the deal-maker, and blew up the heart of the character in vengeance. A surge of wild magic (the new recipient being a level 7 Wild Magic Barbarian/1 Wild Magic Sorcerer) created a new wild-magic heart for the Blood Hunter and everyone was happy with the result. The initial idea upset players - the resolution let them solve it through their own actions, and so resolved the situation.
TLDR: Don't force anything on the players, but let their actions have consequences (how often have we heard this haha).
There may be some groups of players who would enjoy this dilemma, but personally I will never present this to the players.
D&D is a game, and there's an expectation that as players, you can win - or in other words, you can create desirable outcomes. If no outcome is desirable, then what is the point of the game? I have yet to encounter a game scenario where making "the least awful choice" leads to the players feeling satisfied unless they are able to come out of it thinking "this was definitely the right choice, and we were not responsible for lost NPC lives."
I don't think that guilt-laden outcomes should ever be forced on players, and there's always the chance that the players, objecting to being forced into an unwinnable scenario, choose not to care about them.
Since D&D is a fantasy adventure game, I think it's better to go in with a Kobayashi Maru mentality. Present them with an unwinnable scenario, and let them break all of the rules and expectations so that they get to win it.
This is party dependent, my games have always been darker and grittier and my players love that, I never present unwinnable situations but, I do present times when it is clear a decision must be made. One campaign I did put the players in a time loop, to get out one of the things that had to happen was a 10yo boy had to die. The players got to know that boy over the 2 1/2 years of playing time, they got to love his character, they re lived the same 48 hour period a total of 113 times and the last 22 was them trying to figure out how to end the loop and keep him alive. In the end they killed him (he was a vessel for a great evil, the loop was put in place by a powerful being to stop this evils emergence), and the other 2 NPCs that had to die as they where also vessels (a young adult and a much older adult). They then defeated the evil protected the 3 souls and saved them preventing it from rising.
I considered allowing them to save the boy but the whole point of the campaign was sacrifice and living in ignorance. Only the characters knew about the loop at the start of the campaign, they had a choice at the end, go back into the loop ignorant knowing it would continue forever this being trapped but an entire town trapped with it, or destroy it forever but at great cost.
In the post campaign wrap up the players told me they enjoyed the story I told and agree, had I let them “save” the boy then they would have felt cheapened or pandered to.
If the players deserve to feel bad for their actions then let them. There’s nothing wrong with a GM intentionally eliciting a desired emotional response from their players, we do it all the time. Every time they cheer when we wanted them to and we smile, we’ve just done it. There’s nothing even wrong with the emotional response being guilt if they have done something to feel guilty for. But the distinctions between PC (mechanics), character (RP), and player (RPer) is still very significant and far too often overlooked.
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Put yourself in the mind of the monster. I had one player absolutely refuse to attack the goblin priest after he yelled at the players to stop killing their children, taking their treasure and food. Of course their food was human legs. There is a lot you can do when you play the empathy card by the bad guys.
I've had a fair amount of success perplexing players when the bad guy does nothing but talk reasonably at them.
Also begs a think on your game settings culture. Are the consequences guilt (kinda on the player to generate in their PC) or shame/dishonor. The latter becomes an ambience burden the DM has more latitude and agency in imposing, but presumes a different moral foundation than a guilt driven character presumption. I remember the old Battletech fictions had lots of inspiration on how to contend with being a dishonored protagonist and the like.
Getting the players to role play "my god, what have I done?" is a lot harder to pull off in my opinion.
Jander Sunstar is the thinking person's Drizzt, fight me.
That’s easy, just give them a beautiful car, house and wife.
I’ll just show myself out.
Characters shouldn't be made to feel guilty, that should be a choice for the player.
Guilt/regret is also something that is much harder to judge than whether both the players and characters will be happy if they beat the evil dragon. If you know your group well enough and are absolutely sure they'll be ok with it then that's a call that can be made, but it's much more likely to be wrong. Nearly every post that describes having done this in this thread revolves around the killing of a child (including my own, though the child isn't dead in mine and the player can still save the child). I know that my players would absolutely hate the other examples given.
Part of the reason guilty outcomes should not be forced is that either the player has to alter their character's personality to match the DM's design, or they have to decide they simply don't feel remorse (which again may be a change).
Personally I think that if you only offer "the lesser of two evils" then the PCs are being railroaded, there's just a branch in the track. Going Kobayashi Maru allows the players to do whatever they want, even if they fail. Not long ago I ran the siege of a monastery against 3 airships and an army. The PCs could choose to defend the gatehouse, the temple, the stairs to a dungeon, or the civilian area. Depending on which area they did first, events would be different in the other areas they then went to. There was a complex chart for the battle's progression depending on the order they assisted the defenders in (e.g. they don't defend the gate from giants in phase 1, so in phase 2 the giants control the gate, by phase 3 more enemies enter the gate), and there would only be time to go to 3 out of 4.
My players ignored everything I'd planned, cast Fly, flew up and attacked the flagship head on and took it out. This then caused ripples. I was totally surprised by it, and it's the best thing that's ever happened in my game.