How to improve D&D roleplaying

D&D roleplaying

D&D roleplaying is simply playing a character right? Or is there more to it? I believe that there is far more that you can do with roleplay than just play a character.

D&D roleplaying includes pretending to play a character but it is much more than that. It is changing the story based on interactions, and so much more.

We will first cover the basics of roleplaying and how to get into it. After this we will go onto how you can improve roleplaying in your D&D game and teach you many ways to use roleplaying.

Getting into character

The most basic form of roleplay that people think of is roleplaying a character. In order to do this all you need to do is step into someone else’s shoes and act as they do right? Well we have a whole career built around this. It is called acting.

If you really want to improve your roleplaying skills then I would suggest looking into acting. This is the most basic part of roleplaying. Once you are able to act out emotions that are not necessarily yours and pretend to be someone else you have achieved the basics of roleplaying.

Is that all? Well, no. Some actors are better than others. This is not just because they can show a bit more emotion or truly understand a character. Good actors are able to implement better techniques than bad actors.

One such technique is showing emotion through their eyes instead of trying to use every muscle in their face. Another is that good actors have practiced and know what expressions look fake while others just try to act out expressions and are far less successful.

Roleplaying also has different techniques and levels of difficulty to master.

The very first is getting into character.

In order to get into character you have to intimately know your character. Any good roleplayer can do this given time, but they need time. No one picks up a new character and knows how to perfectly play them. That is why the first few sessions of a campaign are not as good as future sessions.

You can still have fun in the first few sessions but players are trying to figure out their characters. What would a character do in a situation where they have to decide between their two most valued comrades? Questions like these need a familiarity with your character to answer correctly.

The first step in getting this familiar is to make your character and provide insights into their personality. D&D 5e does this very well with the background section, but you can go even further.

Consider why that person got their. What morals, core values, and personality traits led them to this point.

But how should we make a character?

Making a character with personality.

Instead of just acting you are also creating a character. In this instance, you are both writer and actor. In order to be able to act, you must first have a character. Let’s delve into how to create a character.

We covered the basics above with morals, core values, and traits, but how do you go about developing those? Take a look at yourself. How did you develop your morals, values, and traits? Were they because of the environment, parents, society, what shaped you?

After you take a look at yourself you can take a hard look at the character you have just scribbled out. Why did you become an adventurer since most people are not? How does this decision effect you and how does it change you from others?

Are your own values and morals different from leading this type of life? What choice did you make to lead you here? Do you regret anything?

I have just bombarded you with questions and no answers. That is because you need to answer these questions before you even play. Once you answer these questions then you can start getting into character as described above.

One great way to start making your character with roleplay in mind is to give them something that makes them stand out. This can be as simple as a quirk, but there should be more to it than that.

Dungeon masters can get away with being lazy and only giving NPCs quirks, but players need to do more. There has to be a reason for the quirk or thing that stands out and it cannot be the character’s defining trait.

You need to have more when you create a character. Give them emotions, reasons, and think about how that quirk effected the character as they lived their lives. Does the character view the quirk as a good or bad thing and why?

As you can see making your character is just a game of 30 questions or more. If you ask and answer these questions though, roleplaying will be far easier. In fact, I would say that you are almost able to put on a new skin.

Putting on a new skin

As you become more familiar with this character you will start to envision yourself as them. You make decisions based on what the character wants and discard all of your desires. This is when you put on a new skin.

When a person does this there are some possible side effects. Good roleplayers who do this have had that character they play every week influence their behavior. Some feel dumber, more introverted, etc if they put on a new skin for hours every week.

I have felt these side effects too, but they go away in a bit. Just something to be aware of.

When you put on a new skin you take D&D roleplaying to a whole new level. You don’t need to act as much because you kind of are that other person. You understand why they do their actions even if you cannot explain it, and do things that you wouldn’t normally do.

Putting on a new skin is an odd phenomenon. You change how you would normally view things. Actions are different than normal and even to a degree morals can be changed.

Putting on a new skin is one way how we get into character, but there are more ways. I would highly suggest looking at what actors do to get into character if you are interested in this topic, but let’s talk about the many unique ways that roleplay can be used in D&D.

Changing the story

” I know that you have killed an uncountable number of innocents. But instead of killing you, I am going to have you repent under our watch.”

This might be something that a lawful good character would do but oh boy. If you have ever had a person pull this the players are confused, the dungeon master is confused, and the game takes a huge turn.

Instead of finishing a story thread you now have to deal with something completely new. Instead of something so ridiculous, lets look at this example.

“I do not want to give this other person the credit. I am not a good guy and will get my reward. No? Then the town will burn!”

This is the player going full murder hobo on the town. Most of the time we do not want to go and become murder hobos, but sometimes players and people just snap. In these instances you have an extremely powerful person snap at some injustice done to them. Should they kill and destroy? No, but it is understandable.

These instances and many more are when you change the course of the campaign. You will not change the game through doing things mechanically well. You will not change the game through the biggest numbers. The only way to change the course of the entire game is through roleplay.

When you have D&D roleplaying change the very course of the game it makes the game extremely interesting. People who just want to follow the plot and have no agency are not roleplaying. This is actually quite boring.

Everything goes according to plan, nothing is surprising, and people just want to go along for a ride. They want to play a video game.

D&D is more than a video game. You are able to shape the world around you and interact with the story. You can change everything! This is why D&D roleplaying is so amazing. Nothing else offers this degree of versatility. It is where the game truly comes alive.

Roleplaying can also effect more minor instances in the story.

Roleplay effecting skill checks

When you have D&D roleplaying happen it should affect other things around you. If you are kind and benevolent it should make your skill checks for persuasion and diplomatic conversations easier.

On the opposite end an unkempt and aggressive player should make persuasion and diplomatic conversations more difficult, but intimidation checks easier.

How you play should effect the outcome.

When a player talks to a person and is caught pick pocketing them does the persuasion roll change? Well, it should change to an automatic fail.

But they were still talking right? So they should just carry on with the roll, make the deal, and then deal with the pick pocketing situation.

Believe it or not people have tried to make this argument that roleplay and situation should have no bearing on rolls.

This is absolutely absurd.

If a person is roleplaying in a positive manner it should help them in their endeavors. If the player is acting in a negative manner it should harm their endeavors.

These are all out of combat ways to roleplay and that is all fine and dandy but what about in combat? Can you roleplay in combat?

Roleplaying in combat

D&D roleplaying is not just restricted to social situations.

It is possible to roleplay in combat. Should the roleplayer receive actual bonuses? Eh…. that is a much more debatable and subjective subject.

If a player has massacred the rest of their enemies friends and licks the blood off their sword, they probably should get a bonus to their intimidate check. In fact, if the massacre was particularly brutal or one sided I might give that player advantage.

On the flip side, I would give the player disadvantage if they were trying to be friends with someone who just lost everyone to you murdering them.

Both of these situations were at the end of combat, but what about D&D roleplaying in the thick of combat? Here I would suggest most of the time to not give bonuses for roleplaying.

“I extra quietly sneak behind the barrel.” Does not get a pass. In fact, most things do not get a pass for gaining an in combat advantage.

You can try to give in combat advantages for roleplaying if you are doing advanced combats as this article describes, but for those of us who are not you can still roleplay.

In movies, we have little quips all the time going on to entertain the viewers. Why not add these in your game. Initiate the quips at your players and see if they take the bait. If they do not then after 1 or 2 rounds let it gracefully die. No one will notice. It surprised me at first but most groups forget about these quips unless you constantly bring them up.

The last way to add detail through combat is through description.

Description in combat.

I have many articles dedicated to talking about this subject but here is the rundown.

“You swing at the goblin and cleave into it’s shoulder. The goblin’s eyes grow wide with fear as you can see it begging ‘please don’t kill me!'”

This gives your player the ability to make a choice as described above. Do they kill a goblin because they should or do they let it run? Will there be after-effects like realizing that adventuring is a terrible line of work that does involve murder and horrors?

Just body language can be used in D&D roleplaying during combat. But how should you reward exceptional roleplaying?

Rewarding exceptional roleplaying

When one player shines above the others and does something amazing, how do you reward them? Do you give them extra experience? A magic item? What?

I have seen people try all of these and have done so myself. It never goes well.

I will talk about how you should not force people to roleplay. If you are giving powerful items, exp, gold, or whatever then others feel forced to roleplay. Instead of forcing others we should encourage them to roleplay.

When someone is providing a positive D&D roleplaying experience you still want to reward them and show others that you value this. If you give some reward and show players that you value this sort of behavior others may adopt roleplaying. That is the whole point of this article, so how do we give them a reward that is noticeable without being too powerful?

The best solution that I have found is to give them an inspiration di that lasts until their next long rest.

Advantage or a luck roll is too much. Inspiration is a way that everyone knows you appreciate roleplay and will reward it, but it isn’t going to make too much of a difference. In addition, players often forget that they have the inspiration di.

You can remind them or just let it fade, but I would suggest reminding them when it might count just to reinforce that benefit.

If you have a bard in the party that can provide inspiration I would suggest to make that inspiration less than that bards inspiration di. If the bard is multi classes and will only have 2 levels in bard you might want to just give inspiration as per normal.

On what inspiration di to give I would suggest to give 1 less than the level that the players would normally be able to gain. For example, if a bard is 10-14th level only give players 1d8 instead of 1d10. This way the bard is still better than a subjective bonus.

I would also suggest to not give these bonuses out too frequently. Perhaps 1-2x max a session. Keep it sparse and only reward awesome roleplay.

With all of this, you might be wondering what is the best roleplaying that I have seen to get some inspiration.

Best RP I have seen?

I started out as a dungeon master at 10 and through high school and even early college murder hoboism was all the rage. Roleplay was a fairly new concept that I admittedly have only been able to really get into for the past 6 years.

That being said, my wife at the moment has an extremely memorable roleplaying experience.

My wife is playing a tabaxi glamour bard. This bard…..

The glamour bard will do almost anything for attention. He will steal hats, water his own team mates and bury them to be the center of attention and if bored go roaming around for orphans to be friends with.

Missions can be changed if the bard gets enough attention and this bard is hilarious.

My wife I think at least is a very different and intelligent individual but when she puts on the skin of her character so many ridiculous things happen that constantly change the plot to where I have no idea what is going to happen next.

This has affected the whole party to a point where I don’t know if planning even matters for my group anymore. They all go and do their creative things and sometimes just hop on a boat because ‘screw this place’ even when there are still a ton of enemies and loose threads.

I unfortunately cannot show you these games but we play in a gamestore and have had many onlookers due to their antics. It has inspired others to play Dungeons And Dragons. This is what good roleplay can do.

If you want to watch good roleplay in action, I would suggest that you watch critical role. Season 2 preferably, but those players carry the show. They change the plot, have personalities, and get into those character’s skins uncannily well.

Those are professional actors so it makes sense, but they are a great group to watch if you are interested in roleplaying.

Now onto some cautionary bits of D&D roleplaying that need to be talked about.

Dismissing roleplay

If a player or dungeon master dismisses a person’s attempt at roleplay then it stifles them. When a person wants to make a decision let them. We will talk about limits in a second, but the main thing to take away here is to not just outright dismiss roleplay.

If you are in a more hack and slash Diablo type of game that is fine but let the players still have agency through roleplay. Let them chose what foes to face, where to go, etc.

Normally people don’t want that much player agency in these types of games but some roleplay can only enhance your experience. What if you players discover some new way to fight enemies? What if they change the story and make it into an epic saga?

Never just outright disregard others when they are trying to roleplay in D&D. There are however some instances when D&D roleplaying should have limits.


“I’m just playing my character.”

I want to get these limits to D&D roleplaying out fairly early on because there are some things that you should just not do.

Using roleplay as an excuse for bad behavior is never okay.

You may roleplay a sadistic person, but that doesn’t mean that you need to be that way towards your party. We are all playing a game and that means that there is a social contract at the table. We are playing with each other.

If you make a character who is unable to function in the group because they are too violently, touchy, or steals from the party then don’t play that character. You chose to play that character when you knew it would not be okay. Do not use roleplay as an excuse for yourself!

In addition to this, do not use roleplay as an excuse for real life creepiness. I have seen people use ‘roleplaying’ as an excuse to make other players uncomfortable. This can happen in any variety of ways, but just don’t.

If you are curious about something going too far then ask it in a comment below or ask your group if it is okay. Some groups are more okay with things than others. They might be okay with whatever you are doing but make sure that it is okay first.

All I am asking here is to not use roleplaying as an excuse for crass behavior.

This being said, you also don’t want to force roleplay when others don’t want to.

Don’t force it

If a player is not roleplaying that is okay. Not everyone is able to make D&D roleplaying work or feel comfortable doing it.

If everyone else is roleplaying or the most interesting person at the table is roleplaying (and if anyone is they are) then that person will try roleplay at some point.

This is why I stated earlier to not dismiss roleplay. If a person is bad at it and trying it out that is great. Encourage them but do not subject them to ridicule or they will no longer roleplay.

On the flip side do not tell them to roleplay. Roleplaying is a hard thing to do when you are not used to it. Imagine a person shoving a script into your face and telling you to act. This is very similar to what you are doing if you try to force it.

Encourage players to try roleplaying if they are ready, but don’t be too pushy.


When you have D&D roleplaying it enhances the session. Players make the game come alive and influence the game in so many ways.

Make sure to encourage and reward roleplaying when it happens appropriately and don’t force it. Do not shame others who cannot roleplay and don’t dis encourage those who are trying to roleplay.

Roleplaying can affect how difficult a situation is and should change the difficulty of situations depending on what you do. If you murder someone’s friends it should factor HEAVILY into an intimidation check.

Speaking of murder, you can also roleplay in combat. You may not always get an in-game bonus to do so, but it still makes the game far more interesting.

This has been Wizo and keep rolling!

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