Tips To Avoid Killing Your RP Character's Conversations
Conversations are an important part of the character bonding process, but it's hard to have them when one of the characters is bored, annoyed, or creeped out. So here are some tips to help you keep your character's conversations alive!
Before you even start the game, stop and think about some possible topics your character might be especially interested in talking about. At least a few of these topics should be things that your character regards positively or feels curious about (and not just out of morbid fascination!). Also, there should optimally be at least one topic that your character gets really excited or enthusiastic over (and it doesn't count if that topic is another character).
And for every topic your character refuses to talk about, think up two topics your character would love to talk about. Nothing kills an RP conversation like a character who clams up on a particular topic and won't move on to talking about something else. So if there's anything your character absolutely won't talk about, figure out wht your character will talk about instead.
Design your character to be willing to learn and talk about new and unfamiliar things. Your character doesn't have to be interested in each and every topic ever, but characters who show disinterest or disdain toward pretty much everything are extremely difficult, if not impossible to talk to.
Think about what your character does off-screen/off-page - EG, work/school, hobbies, activities, social life, etc. Is there anything amusing, strange, or otherwise interesting that could have happened that your character might talk about? These might make for good conversation material - or at the very least, might give your character a good way to start a conversation.
Don't start have your character engage in a conversation just to further a goal of yours. If you have your character enter a conversation with a firm goal in mind (EG, "make this character think mine is cool," "help this character's issues," or "make this character see what a great lover mine would be"), you're more likely to end up trying a bit too hard in an offputting way. Let go of expectations and desires, and just let the conversation happen.
The rule that most people love to talk about themselves holds true for many RP characters, too. Though not always, many people's characters will be happy to tell you quite a bit about themselves if you just ask. But be careful - if they seem like they don't want to talk about themselves or answer certain questions, it may be a bad idea to press onward. Nobody likes a busybody encroaching on their space, and it doesn't matter if said busybody is "just trying to help" or "just trying to find out what's wrong." Also, remember that people can and do get bored talking about themselves and usually want to hear something about the other person eventually, so trying to keep a conversation constantly focused on the other character can backfire.
Don't have your character constantly be a downer. Your character doesn't always have to be a happy ball of sunshine, and not every topic of conversation has to be about happy or cheerful things - but if your character is only ever angsty, sad, sullen, broody, etc. and only has unhappy subjects to talk about or is always complaining about how awful everything is, nobody's going to want to talk to your character for long. Try to make sure the positive output outweighs the negative.
Don't make a your character a total snob. It's not much fun to talk to someone who sees everything you're interested in as boring, uncouth, petty, or inferior, or thinks that you are in every way inferior yourself. It's one thing if your character has a few snobby tendencies, but a total snob is not likely to get far.
Don't have your character be a self-centered braggart. Constantly going on about how powerful, smart, talented, badass, evil, or whatever one is and/or going on about one's achievements and victories tends to annoy people and put them off. So does constantly trying to one-up people by mentioning how one did or went through the same thing, only more/bigger/worse/whatever. Try to avoid or at least minimize this kind of thing if you want to keep a conversation rolling. (You might also look at Reasons Your RP Characters Might Look Arrogant & Egotistical, Reasons Your RP Characters Might Look Insecure, and Reasons Your RP Characters Might Look Like Edgy Tryhards.)
Compliments are good - but only up to a point. Having your character recognize the good qualities and achievements of another character is often a good way to show that your character thinks well of and appreciates others. But if your character piles on compliment after compliment - especially for superficial traits or relatively trivial deeds - your character runs the risk of looking insincere or overly obsessed, neither of which are particularly endearing qualities. Basically, if your character spouts off praise like an obsessed fan or a sycophant, it's going too far. (Also see Reasons Your RP Characters Might Be Creepy (In A Bad Way).)
Don't make players have to endlessly guess at what your character might want to to talk about. Pulling passive-aggressive nonsense like eye-rolling, ignoring what the other character says, or going "oookaaaay...?" whenever your character isn't interested in something most likely going to frustrate and bore other players. Instead, make an effort to bring up something your character actually does want to talk about. Same goes for if there's something bothering your character that you want your character to talk about - being too evasive or too indirect for too long might just drive the other player to give up. Make sure you throw other players a bone somewhere.
Don't spill every detail at once. Abruptly vomiting out one's whole life history or every detail about one's interests at one go is just awkward. Have your character give out small bits of information (around or under thirty words can be effective), and leave it up to the other characters to contribute something or ask for more information. If your character is asked for more information, the reply can be a bit longer - but it should stay focused primarily on answering the question asked and not stray off on long-winded tangents. Most of the time, keeping replies under a hundred words - or even fifty - is not amiss.
Don't turn it into an interrogation. Unless one character is supposed to be educating the other, if the "conversation" mainly consists of one character asking questions for another character to answer, it's an interrogation. Even if the questions are asked with innocent intentions, it can still get awkward and even uncomfortable very quickly.
Look out for signs that the other characters are getting bored, annoyed, or uncomfortable. If the their responses are extremely short (for what's normal for them, anyway - some people are always a bit terse, even when happy or interested!), or if they start trying to talk about something else, it might be time for a topic change.
Ask yourself if what you plan to have your character say invites a response. Put yourself in the shoes of another player for a moment - how might you respond to what you're planning on having your character say? If you can't think of anything, try to think of something else for your character to say.
Sometimes, all you really need to do is just have your character listen. Some characters are really just in need of a good listener. Good listeners remain as nonjudgmental as possible. They don't twist the conversation around to make it about them and their own problems, nor mention that their own problems are just as bad or bigger. They don't tell people that their feelings are wrong or invalid, nor tell them that they should feel differently from how they do now. They might ask questions like "what happened, exactly?" or "why do you feel this way?" or "what leads you to believe this is true?" And if they do offer advice, they only do it after making an effort to understand the full depth of the issue, and even then they offer it more as a possibility or suggestion more than an imperative.
Other pages that might be relevant to you:
Character Interests Generator
Basic Tips To Make Better & More Appealing Roleplaying Characters
General Roleplaying Tips & Advice
Common Problems In Roleplaying Characters
Common Game-Ruining Mistakes Roleplayers Make
Tips To Help You Write Better Roleplay Posts
Reasons Your RP Characters Might Be Bad Friends Or Love Interests
Reasons Your RP Characters Might Be Creepy (In A Bad Way)
More Tips For Portraying Believable, Functional, & Healthy Relationships
Yet More Tips To Portray Believable & Healthy Friendships & Romances
So You Want To Have An Attractive Character?
Tips To Help You Write Better Roleplay Posts
Tips To Be A More Thoughtful & Considerate Roleplayer
How To Spot & Handle Parasitic Roleplayers