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My friend is going to be DMing DnD 3.5 with me and 4 other new players. I want to be the best player I can be.

One thing I have always struggled with is roleplaying. I am an analytical, competitive person by nature; I want to WIN.

When looking at other games & posts on here, I see amazing & creative characters that often have some unique trait or flaw.

In my last campaign, I played a chaotic character and used dice roll to force myself to roleplay a bit (if I roll an 8, I act like a jerk for this interaction).

My problem now is, I want to flesh out my character a bit more and give him personality. It seems like roleplaying will lead your character to make choices that you wouldn't (a bad choice). Doesn't that either mean that you're purposely risking death, or the campaign is easy enough that your decisions don't really matter?

Does anyone have any experience with roleplaying as a competitive player?

To clarify: winning, overall, is making it to the end of the campaign in the best condition possible. Now during a campaign it isn't really realistic to aim for the end in every situation, but there are obviously "good" and "bad" choices. You could choose to kill yourself, for example — I would consider that a "bad" choice that doesn't help me win. If I were playing to win, truly and absolutely, I would be rolling perception, check motive, spot, look, and all the other checks after virtually every action. I would be a cautious and weary player, I would try to avoid fights I think I could not win, and try to never be tricked or caught off guard.

Winning is avoiding mistakes. For example, I meet a wizard in a tavern who gives me a potion, I drink it. The potion is poison and I die. Obviously, if I had rolled a check motive or something, I might have been able to avoid death; I made a mistake.

If I am roleplaying a trusting idiot, my character would never roll check motive, and I would die because of it.

The wizard randomly handing deadly poison to a character is an extreme example to make a point.

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D&D grew out of tactical wargaming, and is still heavily influenced by that. If you want to make it more role-play heavy, you need a DM who will actively help you do that. It shouldn't be necessary for you to always call for sense motive and other checks, the DM should ask for them and, if he wants to be tricksy, pool them a little ahead so you're not sure what triggers them. A DM who can do that will let you roleplay a reasonably cautious character without it unduly slowing down the game. –  Perkins Sep 2 at 17:56
    
By "pool them ahead" I meant occasionally call for an unneeded check and save that number in a pool to be used later when that check is needed for a non-obvious reason. This eliminates the "hey! I think I just failed a spot check!" effect without requiring the players always be making checks just in case, yet still letting them make the rolls themselves. Alternatively, just collect the relevant modifiers for the characters and make the rolls in secret yourself. Different players have different preferences in that regard. –  Perkins Sep 9 at 20:31

10 Answers 10

up vote 25 down vote accepted

I do.
I'm so competitive I managed to win a game of Fiasco (a very non-competitive game).

Luckily, I know why you feel this way and where the source of the problem is.
Unfortunately, D&D 3.X is more often than not the cause of this dicothomy.

There's a thing game designers call reward cycle: encouraging the players to behave in a certain manner by giving them some mechanical advantage if/when they do.
This is done differently in different game where the authors are conscious about the need to encourage the intended behavior with positive reinforcement. Some examples:

  • in the Solar System you get concepts that define your character called keys. following them often puts you into trouble or requires you to be into trouble. You get XP every time you hit a key.
  • in Fate, whenever you do something that's not convenient to your character, you get awarded a fate point you can later spend to reroll, add modifiers to your dice or introduce elements into a scene.
  • in Monsterhearts, you need to get strings on other characters to improve your chances of success. Things that get you strings are not nice things to do to other characters.
  • In Primetime Adventures, players can reward other players when they describe a memorable scene by giving them a fanmail, which can be spent to draw more cards to play against the game master (whoever has more red card wins).

These games make bad choices for your character become good choices for you, encouraging you to play your character's flaws as well as his qualities.
D&D 3.5 also has a reward cycle, but it's not something the authors appear to have planned, unless you want to believe D&D authors actually wanted to encourage playing some psychopats who only care about money and xp.

  • in D&D, you get experience points and gold for killing (or otherwise defeating) monsters, for good roleplaying or for plot-related goals.

Emphasis is because only killing/defeating/avoiding monsters has defined and quantified rules governing the gains. More than that, most of the things you can buy with money or XP are useful to be a better monsterslayer.

In previous editions, you gained XP based on the treasure you could get your hands on: avoiding confrontations meant suffering less HP (or character) losses. Now, the easy way to solve an encounter is "just kill everything". This means in a D&D game there's a straight path to "winning" the game that requires you to bash monsters in the most efficient way. The most efficient way, as many movie villains will tell you, is to get rid of all emotions and vulnerabilities. Weakness leads to being killed. Dying makes you lose some of the resources you gathered.
Of course, this does not produce a fiction that's satisfying to those who want to tell a "realistic" story, nor to those who want high fantasy, epic or similar results.

What usually happens in a D&D game where being a party of murderhoboes is not the intended result is that people is expected to behave consistently (and rolpelay an actual human being), and whoever can't find where the line lies and balance on it is usually either despised for "not being able to roleplay" or is willingly taking risks and worsening his chances at suceeding.
Someone calls it "role-playing vs. roll-playing".
It might be arguable that an equilibrium point or where none of the two happens exists.

So, what do you do?

  • You can modify your reward cycle, by giving XP only for good roleplaying, but this often means "what the DM thinks is good roleplaying".
  • You can remove this kind of reward. Leveling happens when the story calls for it, and money is given out accordingly. Then you introduce a different reward cycle.
  • Maybe the easiest one, play a game that already has a "good" reward cycle. Buying your friends in could be hard, because of the investment needed to master D&D 3.5 and the fear that every system out there takes the same mastery to learn.
  • Learn how to have fun without aiming at the intended reward cycle, while it's still there. If you manage to do this, please tell me how it's done.
  • Just keep playing psychopaths (but that's not what you want, right?)

@Miniman wrote a comment where he suggested to roleplay a character who wants to make optimal choices himself. I suggest you don't: more often than not, being stuck on finding the optimal choice in-character is a flaw you'd probably try to instinctively avoid, especially when metaplaying is involved and you know a stupid decision of your character would make for a great strategy.
What you don't want to get is a character that behaves in a completely different way in different situations, because the lack of internal coherency hampers the kind of immersion you're currently looking for.

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I think that reducing the entire question of roleplaying down to "well, but the XP system rewards kill" is, while true, a significantly incomplete exploration of the topic. –  mxyzplk Aug 12 at 16:51
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My own experience made me think primarily about this. I've uplvooted other answers giving good advice or facing the problem from a different side. –  Zachiel Aug 12 at 17:00
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Even inside the D&D 3.X systems, there are Story Rewards, Challenge Rewards and Roleplay Rewards - you don't really need to "modify the rewards cycle" or completely stop awarding defeating monsters, just put less emphasis on slaying monsters (also note that you don't have to kill a monster to gain XP for defeating it). So even in D&D / Pathfinder, you don't have to play a psychopath to be successful - it's all about how a group plays it... –  G0BLiN Aug 12 at 18:42
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@G0BLiN my point is, killing is rewarded as much as other options, and is treated as a perfectly cromulent solution, to the point where it's the only one (along with otherwise defeating it) that has quantified rules to assign it, contrapposed to the bolded rewards you name. Let's agree before I edit on this. Meanwhile, I added a word about gold buying items to kill better. –  Zachiel Aug 12 at 20:41

Not necessarily

I've run about a dozen games in the last four years, and in each of them the roleplayers come out on top. Some of them happen to do a little min-maxing on the side (like the troll in Shadowrun who lived up to his race's namesake), but the truth of the matter is that it doesn't really matter.

The rules encourage it

D&D is one of those games where roleplaying can actually be pretty actively encouraged due to the way that classes work. Think about your character enough during character creation, and you'll actually find that you can make some fairly effective characters from that. Keep in mind that you may not wind up a min-maxer, but you can make powerful characters who don't have to be built around charisma alone.

Your GM may encourage you

One thing that I've found in many games that I've played is that roleplaying my character very strongly has almost never come back to bite me. Even in one campaign where I sat out half the missions because of my character's paladin-esque morality (in Shadowrun, no less), and a strong sense of self-preservation, I managed to be one of two survivors (with a massive earning penalty, no less), because the traditional min-max and kill everything strategy is actually going to provide clever GM's with plenty of opportunities to kill you, either because you challenge the wrong foe or because your closet full of skeletons is too big to hide anymore.

On the other hand, if you actively tried to follow a character's path, those who have benefited from your actions will be more likely to come to your aid, especially if they know you're not a mercenary psychopath.

Plus, many games and game master advice sections will encourage giving additional rewards to solid roleplayers, not that that's the only good reason to do so.

Sometimes, your own mind will trick you, and roleplaying can help

If I had a dollar for every time my players (or even myself) got locked in the "I have this on my character sheet, so I can do this", I would retire right now. And I plan to live for another five decades, so that means that I'd be rich. However, roleplaying a character can give you a sense of perspective.

  1. You come into conflict with your environment more often, which means you know your limits.
  2. You'll be better able to work with your fellow party members (sometimes, but I've found it to be true in 90% of cases), because they like your character.
  3. Considering the world from your character's perspective reminds you that dragons view humans as a side dish*.
  4. You're actually more likely to act in your character's self interest. What does killing that mine full of kobolds really get you? Good roleplaying considers the universe—getting the kobolds to sign a peace treaty with the town will probably get you the same rewards, and then you'll have a few buddies who didn't get massacred.

I've found that taking a step back and thinking through the eyes of your character helps you pursue motivation better.

*Not always literally, but you get my point.

Still not sold?

I'm not going to say that you'll always win more for roleplaying, but I will tell you that it makes the experience more satisfying. Part of roleplaying is setting your own win conditions, and as a result you often don't need to "win". Consider an open-ended play environment (in video games these are often things like Dwarf Fortress or the Sims with few or no explicit objectives, and most tabletop games are inherently open-ended, though rigid campaigns may not be). You can get by with "winning" by being the most efficient you can be, and simply managing to hang on through each session. However, when I started doing deep character roleplaying I found that I had multiple goals that were based on my character's perspective. It was much more rewarding than simply "now we killed those bandits, so everyone got XP", because I was able to pursue additional goals and have meaningful results.

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+1 for pointing out that roleplaying only puts you at a disadvantage if your goal is incompatible with roleplaying; With any goal that roleplaying will help with, it's an advantage. –  GMJoe Aug 12 at 4:40

It depends of your group's conception of RPGs.

What is winning?

Win what? Win who?

Most RPGs differ from boardgames in the winning concept. There isn't an end square, there aren't winning conditions, there is no endgame. There are only infinite possibilities and choices your character can make.

The GM is not there to beat you, nor you to beat your GM. It would be too easy to kill the whole party if he wanted. The GM can challenge you with perils and disgraces, but that should only serve to make the game more interesting and your achievements more rewarding (in a personal way).

So, what is winning on those games? First of all, winning is having fun. I know it may sound lame for such a competitive person, but it's true. If everyone had fun during the game session, that's the best indicator that the game went well.

Then, what is more fun? An optimized killer without personality, or a motivated character with interesting goals and some flaws that get him into trouble? A game about killing everything or a compelling and rich story? Maybe right now killing and winning XP and gold seems fun, or even funnier than roleplaying and story, but the former gets old quicker than the later. There is a limited number of orcs and traps you can best before it gets boring.

The second concept of winning would be achieving your character's goals. And how @KyleWillie explained with detail, roleplaying would provide more goals to achieve, so you can win more.

The third concept of winning would be having protagonism in the story. If you start to look the game as a story, you would like your character to be a protagonist. And players that roleplay make their character more central.

What makes you the best player?

You want to be the best player you can be, but what makes a good one? Tough question, as every player looks for different things on a game.

For me the good player is the one that contributes to a good experience to him and the rest of the group. He has a good backstory, and his interesting interactions makes the story rich and vivid. Even more, he creates hooks to get other player characters involved in the game. His characters are motivated, but their motivations don't annoy the rest of the group.

Want to be the best player? Make sure everyone is having fun!

What is roleplaying?

Rolling a dice to see if your character acts like a jerk is not roleplaying (sounds more like rollplaying). Roleplaying is when your character acts according to his concept and motivations. If you have a well designed character, you know when he acts gently and when he is a jerk.

For instance, your character could be a jerk because he has lost his daughter and the NPC unknowingly makes an unfortunate comment.

Is roleplaying a bad strategy?

Well, sometimes you can make your character do something that is bad to him. That can be fun. If that is fun, that doesn't mean you lose, it means you are challenging yourself, just as the DM challenges you. Are you a competitive player that loves challenges? Challenge yourself!

Most times, though, roleplaying is not about making the wrong decisions. In real life, most people try to get good decisions, so your character don't make hurting actions, unless confronted with a flaw. You usually don't risk death because your character typically wants to live.

In my games, roleplaying can be a big advantage in fact. It grants your character friends. And friends are a key to success in my games. It also helps you obtaining information from your enemies or competitors. A good roleplayer get more connections and information that someone who does not roleplay at all. So, roleplaying is actually a good strategy.


TL;DR

Roleplaying can make your games more fun and memorable. You have some concepts about winning that don't necessarily are the most funny, and that maybe could be revised in the sake of a more interesting game. At least, you should try.

I'm not a competitive player... or person. But I have played with very competitive players, and in the end, they learned how to make fun of roleplaying and story involvement.

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But their concepts of winning are fun to the questioner –  Phil Aug 12 at 8:45
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@Phil I do not doubt it. I suggest maybe roleplaying is more fun, or at least it doesn't get old so quick. –  Flamma Aug 12 at 9:54
    
This seems to assume that there is one definition of fun when there are many, one of which is having the most optimised killer, so it feels like it's not understanding and talking past the problem. –  SevenSidedDie Aug 12 at 17:12
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@SevenSidedDie Not at all. I'm not denying the fun of being the best killer. I am presenting the OP, which seems to not having a lot of experience roleplaying, other ways to understand "winning" and other forms of having fun with the game, even if all decisions are not optimal (in the occasions roleplaying makes you take not optimal actions). –  Flamma Aug 12 at 18:51

How To Roleplay For Fun and Profit

Don't Roleplay Idiots

Does roleplaying inherently put you at a disadvantage?

Absolutely not, unless you are roleplaying a particularly naive or trusting character. Or you are particularly committed to stat playing when it comes to intelligence ("Farfig Newton" has an 8 INT so he could have an 18 STR and so now he is borderline retarded rather than just lacking in common sense).

Roleplaying Is Just Plain Acting

My problem now is I want a to flesh out my character a bit more and give him personality. It seems like roleplaying, will lead your character to make choices that you wouldn't (a bad choice).

Let's define roleplaying. To get all OED up in the hizzy, the Oxford English Dictionary defines roleplaying as:

"The acting out or performance of a particular role, either consciously [..] or unconsciously, in accordance with the perceived expectations of society as regards a person’s behaviour in a particular context."

It also has a second definition, but I bet you can guess what that is.

So, to be clear, roleplaying is acting in some manner that your might not otherwise, at least in part. The "in part" portion is especially pertinent since this means if you are otherwise intelligent and rational, you don't (as previously stated) have to have a character who is a moron (e.g. they make good decisions and use their abilities wisely). James Bond, for the most part, makes far better decisions that the actors who play him would in similar circumstances.

Life Is But A Stage

Doesn't that either mean that you're purposely risking death, or the campaign is easy enough that your decisions don't really matter?

Frankly, I always thought risking death was an adventure. ;-) As for your decisions making a difference to the campaign, that is solely up to the GM. He or she can offer you up a life-and-death scenario or ask you to pick up a copper piece and make the entire game hinge around either decision (or not).

Admittedly, good GMs in my not-so-humble opinion will give you dramatic decisions with severe consequences, but again, that has nothing to do with roleplaying in the long run unless the GM is trying to tie it in with your character's personality specifically.

Winners Don't Snort Unicorn Poo -- Or Roleplay Idiots

[W]inning, overall, is making it to the end of the campaign in the best condition possible.

Ayup, totally agree... though I would say there is some merit to the "fun is winning" philosophy in @Flamma's answer (allowing that fun can be had besides making the best decisions every time -- if you make no mistakes, there are no truly great tales to tell, I think).

If you like to min/max, or create winning characters, you can still roleplay Despair, a sexy dark elf who gets her way by sleeping around, extortion and otherwise convincing other people to fight on her behalf ("Look Ma! I still got all my HP!") vs. Grog Kneebiter, a crusty dwarf who is nigh-invincible in combat and is often mistaken for a short golem made from a cannonball.

These characters can both be intelligent, rational and "win", just in separate ways (with separate personalities). That is, they can both "mak[e] it to the end of the campaign in the best condition possible."

Grill of Perfection +1

WINNING is avoiding mistakes.

To respectfully disagree, winning is avoiding most mistakes. If you don't make mistakes, life gets very boring. In a roleplaying game, mistakes lead to interesting adventures (at least if you have a GM worth his or her salt). I think the proper phrasing would be something like "learn to enjoy the ride." If making mistakes isn't fun, I would try to stop making them. :-)

Seriously, though, if you are that competitive, you might want to try roleplaying mistake-making characters as a form of game therapy. I would venture to say that being more relaxed at a game session regarding in-game events is far funner than worrying about min/maxing every encounter (even if your overall goal is to "win") -- at least if you can swing it with your personality.

Don't Feed the Tarrasque, Please

I meet a wizard in a tavern who gives me a potion, I drink it. The potion is poison and I die. Obviously, if I had rolled a check motive or something, I might have been able to avoid death; I made a mistake.

Again, respectfully, I disagree. The character was an idiot. Even children are taught not to accept gingerbread from witches. Having a healthy dose of skepticism is expected as an adventurer. Those that don't have this don't tend to live very long (unless you are playing a really lucky character). I can be Friendly Smurf or Grumpy Smurf and not trust scraggly wizards in a tavern.

If I am roleplaying a trusting idiot, my character would never roll check motive, and I would die because of it.

"And I said it once before but it bears repeating" -- don't play trusting idiots then.

The Bottom Line (a.k.a Did I Mention That Thing About Not Roleplaying Idiots? ;-) )

Your character is only as weak as you make him or her.

My personal opinion is that roleplaying characters with flaws adds to a game but honestly, it shouldn't suck all the enjoyment out of playing. My suggestion would be to try and create either:

  • A) A character who is fairly flawless and simply give them a personality different from your own (distinct but still analytical and/or competitive).

  • B) Select a minor flaw your comfortable with (you can start with just one, honest) and balance it out to the point where it can be easily overcome (so you can "win") but still gives the opportunity to create interesting roleplaying situations (you will have to use your imagination on this one).

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Although note in the question, "will lead your character to make choices that you wouldn't (a bad choice)". If the questioner honestly believes that anyone who differs from him is an idiot, then a rule not to play idiots is a lot more restrictive than if he's a bit more... welcoming of diversity ;-) –  Steve Jessop Aug 13 at 14:59

Depends on the GM.

Some GMs delight in trapping players. They set up traps, everywhere, like a lost little girl that is actually a monster, and various other things that 'normal people' would be caught by and players who play cautiously and carefully and in a very optimized fashion tend to do better against those sorts of traps.

It's a really weird style of gaming that I don't get at all. I think it has something to do with the GM vs players thing? Honestly I don't see the appeal.

Some GMs don't really make their worlds interactable. IF you give your gold to the church, the net effect is - you have less gold. If you save the woman despite it taking longer, when you get to the Arch-Sorcerer he is now - harder to fight. Etc etc. The value of reputation, of morale, and of the heroic arc are lost on these GMs who play things by the numbers.

Other GMs, though, will give to roleplaying what I like to call asymmetric reward. Acting in character will cause you to do things that will create opportunities for you, either mechanical (you chatted some thieves cant with the thief earlier, now he grudgingly shows you the secret passage, having seen the horror of the dungeons you receive a +2 circumstance bonus to saving throws against the Dark Lord's spells etc) or further opportunities for roleplaying (it's the great hero Maccaulay! Quickly, let us shower him with young women and ale!).

So, whether or not it puts you at a disadvantage depends on the game. In some games, it definitely does. In others, it doesn't. In some, it is rewarded.


Ultimately, though, playing a character, whatever that character's nature (flawed or unflawed, cold and unfeeling and mercenary or warm-hearted and loving) is actually worth doing in terms of fun regardless of the GM. It spices up boring moments in the game and lets you relate to the game world a lot more - even without the roleplaying leading to Opportunities to Further The Plot, it's still rewarding to the player.

I often game with people who are like you are describing yourself to be - I find that while they don't see a benefit immediately to roleplaying, after managing to get the hang of it they see the benefits and start doing it a lot more. This has even been at tables where the GM actively discouraged playing to character by setting metagamed traps for players who did so. I think that if you push yourself and really go for it, you'll find out why other people do it - namely, that it is awesomely amazingly fun.

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Play your character like a real person!

I'm also a quite competitive player - what I see as a win in a roleplay game? If my character achieves his goals! That doesn't have to be winning a quest, killing an enemy, getting all the Gold an XP, but real in-game goals for the character!

And if you character has some predefined goals, he will do everything to reach them. His actions and the percieved character of his evil/good/crazy/relentless/lazy shouldn't be traits I have to fight with like hindrances to win the game, but rather traits which result from his personal goals!

Just think about why real people are how they are - and they're living their best everyday, but still some of them are lazy bums, other reckless idiots and psychopaths. You just have to define your goal accordingly:

If your character is a lazy bum, then your goal of winning the game should be: Lead an easy life, get through the encounters with the least effort and try to secure enough gold so you can settle with the beautiful towngirl over there. If your character is a little chaotic and evil, your goal should be to do some evil things...

Just think of it like this: If life was a board-game, you would get satisfaction-points for everything you do which makes you happy, follows your needs,whims and desires. So think about collecting the most satisfaction points with your character, for action that lie in his interests! And you will play him like a real person, following his interests and needs and maybe winning the game by becoming king, or by sacrificing his soul (or his adventure party, if his groups likes PvP) to an evil god, or by living through amazing adventures without too much risk for his life, or by dying to defend his believs and moral standards

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The notion that you cannot simultaneously optimize and roleplay is known as the Stormwind Fallacy, that is, widely recognized (and named!) as an inaccurate statement. If anyone tells you that you cannot do both, you should ignore them. Their narrow-minded insults are not worth considering.

The Stormwind Fallacy is often extended to the statement that roleplaying and optimization are mutually independent, that is, how much you roleplay has zero effect on how much you optimize, and vice versa. This is a harder statement to make, and becomes a question of definition.

What is optimization?

The big question for whether the “stronger” form of the Stormwind fallacy is, in fact, fallacious is what you mean by “optimizing.” Within D&D 3.5, it is possible to become literally capable of doing anything, instantaneously, at level 1. Powers dramatically exceeding those attributed to the gods in the setting. The particular tricks that enables this have themselves been optimized for executing the tricks as quickly as possible, since the only time such a character is vulnerable is before they have completed it.

This is what is known as “theoretical optimization.” Theoretical because it is never intended to be used in a game; there would be no point. TO, as it’s known, is its own separate game from D&D, for all it is based on D&D’s rules. It’s a game of playing with, abusing, and stretching those rules and seeing how badly you mess things up. Pun-pun, described above, gets infinite or as-large-as-he-likes stats for everything, every ability ever published, and arguably can start making up his own. That’s the extreme. The TO game, itself, is often played with various “houserules” – restrictions on what you can do to make it a little more interesting. Commonly, no infinite loops, for example.

But this has little and less to do with D&D 3.5. It’s a different game, and is not related to how you play D&D. Optimization for a game of D&D, rather than theoretical optimization as its own separate game, is sometimes known as “practical optimization,” but more frequently just simply optimization. This distinction is very important.

Theoretical optimization limits roleplaying. Pun-pun can never be challenged in any meaningful way, and while you certainly can roleplay a god-like being like Pun-pun, and roleplay him well, he is still just one character; if you define optimizing as literally doing everything you can, the logical conclusion is to always play Pun-pun. Wouldn’t, I’d argue, automatically mean you’re roleplaying badly, but it does have an effect.

“Real” optimization: optimizing for constraints

But practical optimization is optimizing for a purpose. Within engineering, optimization problems are defined by their constraints: the reason why there is an optimal answer is because constraints prevent you from going beyond whatever that optimal answer is. So what constraints do we have?

There are two: the constraints applied by your table and group (gentlemen’s agreements, houserules, expected power levels, setting and themes, and so on), and the constraints applied by your character.

Group and game constraints

You should see the expectations of the group you play with and the game you are playing as constraints on what your character can do. Even if your character would be better using some third-party sci-fi book’s futuristic weaponry, you can’t use them if you’re playing in a high-fantasy game with people using only official material. Even if a series of tricks would mean your wizard has phenomenal cosmic powers, you can’t use them if you’re playing a game of swords and sorcery where magic is rare and evil and real heroes use swords (note: the D&D 3.5 system is, in my opinion, an atrocious choice for such games; the system is kind of built on assuming that wizards do have phenomenal cosmic powers).

So that’s one constraint. That’s more about playing the actual game than it is about roleplaying; it’s about showing up to the same table as everyone else and joining with them on the quest. Without that, you’re playing different games and the friction from that will cause problems – and if you are the one ignoring the constraints, you are in the wrong, and best case scenario you have to retire the character and start over; worst case scenario you’re kicked out of the group.

Character constraints

The other constraints are based on your character, and are much more tightly tied to roleplaying. Your character should have goals and should have talents – and all “talent” really means is innate interest and tendency. There are certain things your character wants to get done, and there are certain methods that your character gravitates towards for solving his problems.

In Dungeons and Dragons, goals typically involve delving into a dungeon and slaying a dragon – that is, going on some epic quest of danger and being a hero that through wit, ingenuity, and more than a little combat skill, overcomes those dangers, completes the quest, kills or otherwise defeats the Big Bad Evil Guy, and saves the world/the girl/the MacGuffin. There are sub-goals and side-goals and maybe that’s not what the character originally set out to do, but ultimately this is what the game is about and what the system is designed to support.

There are, of course, variations you can apply (maybe you are the Big Bad Evil Guy, so you kill the hero and overcome the forces of good, and take over the world or whatever), but straying too far from the formula tends to cause various problems (e.g. a pacifist is a problem, because the system has very detailed rules for combat, which you’re no longer using, while having very simplistic rules for non-combat that tend to be an unsatisfying focus; a system that is better at non-combat situations would be a better choice for that character).

But the point is, ultimately your character is going to have to face danger, and almost certainly is going to have to use force to overcome at least parts of that danger.

So how is your character going to do that? Will he enroll in an arcane university, unraveling the secrets of the universe? Maybe that was in itself his original goal, just to learn magic for magic’s sake, and then plot happened and now he has to face danger. That’s fine. But maybe instead your character will take up her father’s sword and set out to save her kidnapped little brother, and never consider wasting time in a school. Maybe your character grew up on the streets, and was making a simple “honest” living as a pickpocket when he found himself where he shouldn’t have been, was caught overhearing something he shouldn’t have, or stole the wrong thing, and now has an evil cult hounding him and his desperate attempts just to get them to leave him alone lead to him leading the resistance against their plans for world domination.

Each of these characters is good at different things. Your character is going to be good at one of these, or something else entirely. But the point is, your character has a real problem to solve, and he or she is going to want to solve it as well as they can. They are going to want to use the skills they are good at and then get as good as they can be at them. That’s just how heroes react to having critically important quests of great danger thrust upon them.

So whatever it is that you do, and whatever it is that you want to achieve, you are a hero (or a great villain), and you’re going to want to do it right. In-character, you are going to optimize your skills. And this is the reason why there is no need for any conflict between roleplaying and practical optimization. People don’t consciously go into danger with suboptimal gear or skills, when they’re fully aware of other options that are just better and cost the same thing.

So this is how you should optimize: you are making your character the best that they can be. They exist in a world (remember the group and game constraints), they have their own interests and talents, so best is defined differently for them than it would be for another character in another game, but nonetheless, within those constraints, optimizing is making that character the best he could be.

And that’s good for roleplaying, too. When you want to roleplay a master swordsman, it’s important that you actually have strong swording skills. If the dude who just picked up a sword because he needed something is as good, or better than your master swordsman, you have a problem that’s going to negatively impact your roleplaying. And unfortunately, within D&D 3.5, that situation is all too likely to occur.

Conclusion

D&D is about heroic fantasy, and heroes react to dangerous quests by meeting the challenge, training and equipping themselves for the quest, and being prepared. In other words, the choices you make to optimize your character, provided that they fall within the constraints of the group and game, as well as of the character him- or herself, are very likely the choices that your character would have made, as well. Thus, there is a lack of friction between roleplaying and optimization: both want the same thing, so long as you are cognizant of the constraints.

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I have deleted this conversation as it was not constructive. Please be nice, and remember that comments are there to improve the quality of our questions and answers, not start fights. –  C. Ross Aug 12 at 16:23
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It may be worth noting that the Stormwind fallacy is a very strong statement (A and B are incompatible = false), so it isn't a direct demonstration that weaker statements (A and B are compatible but interfere with each other; A and B require compromises) are false, but is relevant for discussion of those because it means A and B are compatible. –  SevenSidedDie Aug 12 at 16:41
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This seems to be entirely addressing build-time optimization (with a big ol' chip on your shoulder) and giving short shrift to actual in game activity, which is more what the OP is asking about. –  mxyzplk Aug 12 at 16:53
    
@SevenSidedDie If I've understood you correctly, then yes, I agree. I intended to establish that with my first two paragraphs. I start with the Stormwind Fallacy as a statement that makes a weak claim (they can be done at the same time) strongly, and work from there about more specific, significant claims about 3.5 as a system and what compromises are or are not necessary between the two. –  KRyan Aug 12 at 17:31
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Oh I see, yeah. I didn't follow the logical connection between those two paragraphs, or the connection between the second and the OP's issue of interference, but I can see it's there. That you're tackling the independence claim to address the interference claim could be brought forward a bit in that introduction. –  SevenSidedDie Aug 12 at 17:40

The thing is, your character can have "flaws" but those flaws can add interest without being "flaws" from a competitive point of view.

Yes being a trusting idiot can get you killed - but if you want to play a trusting idiot team up with a suspicious paranoid. The two of you can play off each other, have a lot of fun, and together balance out each other's quirks.

So the wizard gives you a potion, you go to drink it. In the meantime your paranoid friend uses slight of hand and swaps it for a vial of water. The wizard gets confused as nothing happen, your character is oblivious, all the players get to enjoy the scene...or more simply your friend just says "hey, don't drink that".

More simply though you can have quirks or flaws that are more subtle.

Decide on some "triggers" that set your character off in either a good or a bad way. For example his family was murdered. Now he will go out of his way to protect children and if he hears someone threaten one he'll react. It could be as simple as a serving boy in an inn spills a drink and the customer cuffs the lad. That would then trigger you to jump in and you can have a big shouting match.

It doesn't have to end in a fight, or loss of status, you can just have some fun playing off that quirk of your character.

Being chaotic doesn't mean rolling a dice all the time. It means being unpredictable, or unreliable, or something else that you decide. For example your chaotic character may just hate being restricted. Laws, rules, anything else. if someone says you must do something then you will tend to do the opposite or do whatever you can to subvert the rule. That doesn't mean being stupid though. If the guard tells you "no noise after midnight" you will say "yes sir, no problem, sorry sir, I'll keep the noise down". Then arrange for every cockerel in town to crow continuously for the following night...or for a massive party to happen...or for the temple bells to keep ringing...or whatever else strikes your fancy.

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I'm going to pipe up here and say "It depends upon whether or not you follow all the rules."

The challenge rating system is not set up for just monsters. It does focus on monsters because it's really easy to stat out a monster and give it a CR. It's a lot harder to stat out a CR for a social situation. This is, however, why we have NPC classes, like commoner and noble. Because then we can more easily stat out a CR rating for that character.

What's more, you're familiar with the difference, I hope, between the CR of a monster and the CR of an encounter? Namely: If you have an encounter with an iron golem in a stone canyon, then the CR of the encounter is the same as the CR of the iron golem. However, iron golems are healed by fire. If you have an encounter with an iron golem in a burning building ... the CR is much higher, because the situation is put together very specifically to favor the monster.

In a similar manner, the rules puts together the rules for challenge ratings for social encounters. A level 5 commoner merchant who is trying to cheat you is a CR 5.

Now, let's say that you are playing a particularly gullible character. That level 5 commoner is still a CR 5 creature - but the encounter is a CR 6 or CR 7, because the social landscape - your gullibility - means the encounter is specifically tailored against you, to favor the CR 5 merchant.

Just talk with your DM, and make sure you're getting credit for all your challenges, and bam - you have a new situation on your hands. The focus upon monster-based XP is all well and good, and it is the easiest method of determining xp because it's a pretty black-and-white situation - but there's a lot more to the rules and the system than that. The fact that these rules are here and laid out for developing social challenges is incredibly ignored amongst the community, as far as I've noticed, but Monte Cook, Jonathan Tweet, and Skip Williams were sure to put those rules in. Some of Monte Cook's blogging on the subject really opens up the potential of the rules to stuff other than killing monsters.

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First off, if random wizards in inns are handing out potions and the DM does not suggest a sense motive or somesuch, I have some reservations about your DM. The DM can kill you more or less at any time; it is generally considered unsporting for them to require constant vigilance on the part of the player. Some campaigns also lack a win condition like you seem to be aiming for- does yours have a defined winstate? Most of mine do, and the DM will tell us what it is usually before we make characters. Every character I make in these games has the primary goal of achieving this goal, for varied in-character reasons.

I feel like most of the roleplaying I do is in how to go about achieving the goal. Take the goal of "Kill Lord Puppy-kicker the Dark." One of my characters would have looked at that and thought about how to raise an army large enough to go to war with Puppy-kicker. Another would have thought the best way to do this would be to get enough gold and resources to build and outfit everyone in the party with top of the line magic items. The character I'm playing now would plan to acquire the most deadly of poisons and somehow sneak it into all of Puppy-kicker's breakfast pancakes.

A brief note- it doesn't sound like you're being 100% committed to winning when you make characters. The optimal builds in D&D are pretty well explored. Pun-Pun is the best I've ever heard of, but I know there's an artificer build that's supposed to be able to match him. A perfectly optimal wizard is supposed to be able to solo things that take an entire party of tier three characters by level five or so. (Explanations of class tiers here in case you are unfamiliar with them.) Do you play things other than pun-pun and other first class builds? Do you play non-tier one classes? I'm guessing yes- actually playing Pun-Pun sounds really boring. Like you, I enjoy victory, but after my first CoDzilla cleric I decided I wanted to work a little harder. If you are using optimal tier one builds, then maybe step it down to tier three or four?

I tend to get frustrated making a character with character flaws, like naive trust or a vicious temper. When I follow it, I feel like I set myself up to make dumb choices, and when I don't I get disappointed in myself for not roleplaying. I've gotten better, but when I started I found habits much easier, and I still think they're more characterizing. Do any of your characters smoke? Drum their fingers when they're bored? Read trashy romance novels? Most of my characters speak in an accent of some kind, so I can make it clear when I'm speaking in character or not. Since I can only do three kinds of accents, this means my characters are either Scottish, British, or Russian. Stereotypes can be wonderful jumping points for characterization- my Scottish dwarf lived by the rule "What would Gimli do?" Casual insults to the elf? Check. Totally willing to work with the elf against the bad guy? Check. Serious abuse of alcohol during downtime? Check. None of that impeded my ability to win- I suppose if the DM had been inclined, they could have had someone jump me while I was inebriated. On the other hand, since he never made me save against the alcohol I wasn't taking any penalties from it.

Pick your favourite character from fiction. Build a PC in their rough image, then shamelessly steal every quirk and habit from them that doesn't jeopardize victory. Steal Tony Stark's flirtatiousness and sarcasm, but ignore his habit of alienating his allies. Be Drizzt, but probably not with two-weapon fighting because it just doesn't seem to work as well as a bow. Once you're comfortable in their skin, play around with making up your own habits and quirks. Do you prefer first watch or third watch? They're statistically identical since they get you the same amount of sleep, but one suggests a night owl while the other suggests a morning person. When you show up at the inn, what do you order for food? Do you always order the same darn thing, or do you ask for the special? Have someone cast detect poison either way of course.

Unless you are a hardcore mechanical optimizer, you probably don't need to change any of your mechanical behaviors. Ask the DM if you need to worry about gotchas; I tend to assume if the DM was out to get me I'd be dead anyway due to invisible epic level wizards in the bedroom and trust them to give me a save of some kind before being murdered, you know, make it interesting. Instead, add a bunch of entertaining quirks, and speak in-character as much as possible. Make a remark on each important NPC you meet, be it obsequious or snarky. If a character develops out of that who wants to do sub-optimal things, do them if it sounds more fun than the straight path to victory.

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