Most Common Roleplay Challenges (+ How to Overcome Them)

While there’s no question that it can be fun and thrilling, there are tons of common roleplay challenges that crop up, regardless of your experience level. 

In our comprehensive guide, we’ll tell you what you need to roleplay challenges, including what makes it challenging, the most common difficulties, and how you can overcome these challenges.

Why Is Roleplaying Challenging? 

Whether you’re roleplaying by yourself or in a group, there’s no doubt that roleplaying can be challenging. One of the most difficult parts about roleplaying is the spontaneity and improvisation. The ability to think on your feet and respond doesn’t come easy to everyone. A large part of roleplay is the unexpected scenarios that come with it and your ability to react to them. Plus, folks who’ve never roleplayed before can feel uncomfortable and out of place, especially around more seasoned roleplayers. 

Roleplayers are constantly growing and learning from roleplay challenges, and that’s part of what makes it fun. 

6 Common Roleplay Challenges and How to Deal with Them

Roleplay can be very fun and rewarding, but it also takes dedicated effort and practice to engage in a successful roleplay. Chances are, you’ll come across some challenging situations and moments during a session that can leave you wondering what the best move is. Here are six common roleplay challenges and solutions for how you and your group can overcome them. 

1. Your group has toxic roleplayers.

When you engage in group roleplay — especially when you’re roleplaying with folks you don’t know — there’s always the risk you’ll encounter a toxic roleplayer. Roleplayers who are toxic don’t always have the same traits, so it can be hard to recognize until you’re in the thick of it. It might be someone who struggles with emotional intelligence, empathy, communication skills, or something else entirely. Regardless, toxic roleplayers can create unnecessary drama and negative interactions for the entire group.

If your group is dealing with someone who’s toxic, one option is an open discussion with the person about their problematic behavior. This can be a one-on-one conversation with you and the toxic person to discuss what you’ve noticed and how it’s affected the group. You can even use a tool like the Situation-Behavior-Impact (SBI)™ feedback model to make sure your conversation stays on track. You can also get support and suggestions from other roleplayers who might be dealing with similar situations.  

2. There’s a power imbalance (or a power struggle).

When you’re participating in a group roleplay, it’s not uncommon for there to be power struggles. Even with roleplaying games like Dungeons & Dragons where there’s a designated “leader,” the Dungeon Master, sometimes players still struggle to accept their roles and responsibilities. 

If your group has trouble with power imbalances, encourage everyone to openly discuss any problems or concerns they have. Make sure they know the group is a safe space with open, respectful dialogue. If worse comes to worst, you can always find someone to mediate the conversation. Having a neutral mediator can help resolve conflict more easily. 

3. You’re having trouble scheduling folks for a roleplay session. 

One of the most common roleplay challenges, hands down, is scheduling conflicts. Whenever you engage in group roleplay, you have to work with the schedules of multiple people, which often leads to conflict. Many people who roleplay are also balancing other time commitments, like school, work, or other activities. It can be hard to organize a group together when everyone has different commitments. Not only that, but many roleplay groups have folks in different time zones, which can also complicate things. 

If you’re in charge of scheduling group roleplay sessions, try to be as accommodating and flexible as you can. Having a group chat over text or using apps like GroupMe or Discord can make coordinating easier. Once you have a set time and date, you can even use something as simple as Google Calendar to create invites so everyone has the session on their calendar. 

4. You’re struggling to come up with roleplay ideas.

Whether you’re roleplaying individually or in a group, having trouble coming up with roleplay ideas is something that everyone experiences. Many people experience writer’s block, struggle with character development and plotline ideas, or simply can’t think of a worthwhile roleplay scenario. It’s a frustrating but completely normal roleplay challenge. The solution will depend on your specific problem. 

For example, if the main issue is you’re struggling with writer’s block, there are tons of exercises that can help you overcome it. Practices like mind mapping, free writing, or general brainstorming can help get the creative juices flowing. However, don’t be afraid to take a step back and take a break if you’re still having trouble. Coming back to it later can give your brain a much-needed rest and make it easier to come up with ideas. 

If you and your fellow roleplayers struggle with character development, take some time to really dig deep into your respective characters. Think about the character’s backstory and their personality traits. What motivates them? What are their strengths and weaknesses? Answering these questions can help you flesh out characters and lead to a more successful roleplaying session. 

5. Your roleplay group is inexperienced.

Although it’s not a problem, having an inexperienced group is one of the most common roleplay challenges out there. Folks who’ve never roleplayed before often struggle with some of the same difficulties, like staying in character, remembering game rules if participating in an RPG, or following basic roleplay etiquette. 

If you’re working with people who are inexperienced roleplayers, remember to be patient, first and foremost. It can be overwhelming and intimidating to work with folks who are seasoned roleplayers when you’re a beginner, so a little patience will go a long way. Doing things like setting clear expectations and fostering a positive roleplay environment will help players feel more comfortable. Offering non-judgemental support and guidance can also make a big difference when it comes to an inexperienced group. 

6. The group has trouble following basic roleplaying etiquette. 

Because roleplay is such a versatile subject, the basic etiquette of each type of roleplay can differ. This can lead to conflict, especially when one behavior might be OK during one type of roleplay but not OK in another roleplay setting. 

For example, in a historical roleplay, folks often dress up as their character in period-appropriate clothing. However, it might cause conflict if you started a Dungeons & Dragons group and expected them to source clothing that would be realistic for their characters.

Even so, there’s basic, often unspoken etiquette that roleplayers expect to follow, and failing to do so can cause issues. To avoid problems with etiquette, be sure to follow some of the basic expectations and unspoken rules for roleplay, such as: 

1. Be respectful during and outside of roleplay sessions
2. Don’t try to control how other people roleplay 
3. Avoid metagaming — AKA, using information you learned out of character during a roleplay while you’re in character
4. Set and keep up important boundaries (more on this below)  

How to Boost Your Roleplaying Abilities With Yoodli

It doesn’t matter if you’re engaging in a creative roleplay with friends or you’re doing a little interview roleplaying to prepare for an upcoming job interview. Regardless of the exact kind of roleplay, a little practice goes a long way. If you have a goal of improving your roleplaying skills, look no further than Yoodli. 

Yoodli — a roleplay and speech coach powered by artificial intelligence — offers folks realistic roleplay scenarios to practice their skills. Anyone can leverage Yoodli to practice roleplaying, whether that’s with one of Yoodli’s existing scenarios or a custom roleplay idea. With this comprehensive tool, there’s an endless amount of possibilities for practice.

It works like this. Yoodli provides a bank of existing roleplay scenarios you can choose from, from sales roleplay calls to media training and small talk (and everything in between!). If you have a specific scenario in mind — say, negotiating for a raise at work — you can use Yoodli’s Builder to create a custom roleplay scenario from scratch. Once you’ve chosen a roleplay scenario, you’ll start the session and Yoodli’s AI persona will engage in roleplaying with you, just like a human would. Plus, there’s a plethora of AI-powered personalities you can roleplay with, so you can get experience chatting with all different kinds of people. 

But after the session is over, it doesn’t just end there. You’ll get an in-depth, personalized report of exactly how you can boost your skills. The actionable feedback you’ll get will help pinpoint exactly what you need to work on and how you can achieve those goals. 

The best part? You can get started with Yoodli for free at https://yoodli.ai/.

Tips for Preventing Common Roleplay Challenges

While it’s true that some roleplay challenges just can’t be prevented, there are steps you can take to set you and your group up for success. Whether you’ve just started a new roleplaying group or you’re considering it, here are some simple tips for preventing common roleplay challenges. 

1. Set boundaries ahead of time.

If you’re doing a solo roleplay session, like prepping for a job interview or practicing an upcoming presentation, setting boundaries is probably the furthest thing from your mind. However, if you’re engaging in a group roleplay, one of the best tips for preventing common roleplay challenges is to set boundaries ahead of time.

Think about what kinds of limits you’d like to set for your group before you pitch them. For example, you could set boundaries for the length and frequency of roleplay sessions. If you’re willing to commit to a 4-hour Dungeons & Dragons session once a week, you can set that expectation for yourself. That way, if the session starts to go over 4 hours, you’ll be well within your rights to exit the session after that time. Nobody will be surprised because you’ve set that boundary ahead of time. 

Whatever your boundaries are, be sure to set those limits and communicate your expectations clearly with the group. Otherwise, things can get lost in translation, which can lead to more roleplay challenges. 

2. Try to be patient and practice empathy.

Regardless of whether you’re a new or a seasoned roleplayer, aim to work on your patience and empathy skills. This is especially true if you’re roleplaying in a group setting with other people. It’s normal to make mistakes, even for experienced roleplayers, so embrace them. 

If you’re playing a roleplaying game that has lots of rules, like Pathfinder, someone is bound to make a mistake sometimes. That’s OK! Making mistakes — especially in group roleplay — is normal and something that everyone can grow from. If you or someone else makes an error during a session, keep a supportive, positive attitude and move forward. 

3. Work on your communication skills.

Even something as simple as a misunderstanding or misinterpretation can lead to more roleplay challenges. To avoid this, take time to sharpen your own communication skills. That means committing to active listening when other roleplayers are talking and using clear, respectful language. 

If you’re working in a roleplaying group with other people, make sure to encourage and foster an open, respectful dialogue. This will lead to more constructive conversations and leaves less room for interpretation and misunderstandings. 

4. Keep an open mind.

Learning how to become more open-minded is a great way to prevent common roleplay challenges. If you’re open to listening to the ideas, perspectives, and opinions of others, it’ll make for a more fruitful roleplay experience for everyone. Being close-minded can lead to unfair power imbalances and it can make it a struggle to come up with new ideas. 

Instead, make it a priority to explore and embrace new views and perspectives. If you’re leading your own roleplay group, encourage feedback from other roleplayers and work on your feedback reception skills. You can use the group’s feedback to improve your own skills and roleplay sessions overall. 

The Main Takeaway 

Roleplaying isn’t always easy, and it’s normal to encounter roleplay challenges from time to time. However, overcoming these challenges is much easier when you have a tool like Yoodli that you can use to practice in a safe, risk-free space.