Is the Game Interesting If the Players Always Win?

Greetings gamers from all systems, places and timelines.

Is a game fun if your players always win? 

In any game, just like in life, no one enjoys constantly losing. Most people would quickly get discouraged and want to move on to another game or stop playing such games at all.

If the players always won, wouldn’t the reverse also be true?

Instead of being frustrated with consistently losing, the players would start phoning in every scene and battle because the chance of defeat is less than zero – if you could keep the players showing up at all. Likewise, the person running the game would probably get bored watching the players handle every problem with an all-out frontal assault.

Some players honestly enjoy this style of game, and I get it. The time between games can feel like forever. When you finally meet up with your crew, everyone wants to kick some ass, tell some jokes, have a cool moment and then go home happy.

The problem is, the level of difficulty the DM and players are seeking may not match up, and these expectations vary greatly from group to group. That’s why I would like to provide some tips on how to make sure losing doesn’t necessarily mean game over, and the DM and players alike can have fun and challenging sessions. 

Defeat at the Castle (Insert Holy Grail Joke Here) 

Now, I want to clarify that I am not talking about defeat in terms of a TPK or a character’s death. What I am talking about is when the mission failed screen comes up in giant red letters.

You know: The caravan the party was protecting gets ransacked, the contact they were trying to find turns up dead, or the BBEG made off with the crown jewels. But even the best gamers I have ever met knew that, while they may put together a solid plan, it may not work.

And, honestly, isn’t that half the fun?

Some things should occur that the party had not taken into consideration, like the party rogue blowing their stealth check even after burning a DM inspiration. However, some of the most memorable moments in my past and even recent gaming took place from seemingly random moments that no one, including myself, who was running the game, expected.

As long as these unexpected moments are consistent and fit with the continuity of the game you are running, they should be the insults that drive the party to future success. Otherwise, that scene where something unexpectedly good happens won’t have any mystery to it and come more off like part of a poorly directed movie. 

Being Brave vs Fearless 

When a player creates a character, they make an extension of their own personality that turns them into a superhero. So, odds are, they want to send them out into the world and make their stories into legends.

However, as the DM, you may want to establish in game zero that there is a difference between a character who is brave and one who is simply reckless. Because the reckless character is the one who sucks the party into encounters the players have no business being involved with (at least at that level). This could range from anything from calling the thief boss out on their bullshit to shooting an arrow into the monster with a CR rating 5X higher than the party.

The problem here is you don’t want to necessarily punish players, especially the ones who didn’t start the mess. However, you have to play the ball where it lies because, if there are no repercussions for these actions, you will definitely see the same player (and soon others in that group) pulling the same kind of antics. And, as DM Thorin once said, “ It’s not my job to keep anyone alive.” 

When the Quest Gets Botched  

In one of my previous articles, we established that death is a necessary component of any TTRPG. Just like death, the threat of defeat must be real.

The question is, how should it be presented so your players don’t want to take you outside and frag you at the end of the session?

First, the defeat should be fair and handled within the boundaries of how things have operated within the campaign so far. (So, be consistent.)  If something about their defeat doesn’t make sense to the players, and you can’t simply explain the details because they don’t have all of the pieces of the puzzle, hint to them that they are missing something.  However, be ready to reveal this information later and give them a chance to uncover it. (A little bit of mystery can go a long way.)

Also, it is probably best not to hinge an important plan or encounter on a single die roll because that is exactly how characters died all day long in previous editions of D&D. But, if the plan does revolve around one or two rolls, advise the group of the chances of failure and roll those dice where everyone can see them. A plan can have an excellent chance of success and still go so far south that the party finds themselves standing in the jungles of Chult. (And we’ve all been there!) 

Conclusion 

One of the best things about D&D is that the story takes place in a structured world with rules, boundaries and dice mechanics to add a critical random element that keeps it from turning into a novel. Even if the players wanted to play in a novel and they were handed scripts at the beginning of every session, only the author would how it ends.

In some respects, “winning” is a lot like the DM awarding treasure. If you do it too often or too easily, then it will just be expected and lose any real meaning. The players should have their chances to be heroes, have cool moments and play out those characters they brought forth from their imaginations. However, victories should be earned, not expected, or the campaign will risk losing the interest of its players.