Roleplaying a charismatic character

[TakeitVillain]

This is for a dnd 5e game, but anyone skilled roleplayer should be able to help me out. I'll cut to the chase. I just started playing an aasimar swashbuckler rogue, who's meant to be a charming character (Expertise in Persuasion and Deception). However, oftentimes whenever I spoke in character, it was pretty stupid or not how I intended. Our campaign is a dark intrigue sort of game that is very roleplay and consequence heavy. (We speak in character via accents btw).
It's been giving me social anxiety.
What's your tips for roleplaying this challenging situation? Help a girl out!

[Koo Rehtorb]

It's not going to be particularly easy to play someone more eloquent and charismatic than you are. I think a useful tip to fake it though is try speaking less, but better. If you can't think of something charismatic to say, say nothing. Coming off as brooding is better than saying something dumb and coming off as a joke. Put your effort into making the lines you do speak better ones.

[Calen]

Try watching some movies with characters that are similar to your character. Maybe its Jack Sparrow, maybe Han Solo. Maybe collect some quotes on a page so that you can pull off a witty line without flubbing it. (I rely on this one a lot.)

If you are completely lost on what to say you can try pulling it back to third person a bit.
Instead of 'I go up to the knight and say. "Ah most excellent knight your help is like the sunset...because" [insert a mental curse because you realized you messed up].
Try instead, 'I go up to the knight and layer on some praise for the help that they gave us.'
I dont recommend this all the time but I'll use it in pinch.

[sktarq]

Well...best advice I have for you is...

Don't

and by that I don't mean that you should avoid playing characters with Cha scores higher than your own (I mean imagine if we said that for Strength?) but handle your higher Cha score like you would a higher Strength score...you let the dice handle the technique. I mean I know little of how to swing a bastard sword but nobody has an issue when the dice are used for my character to do it so why would persuade be a skill that the PLAYER needs to know?

and as part of the same logic. My pal who DOES know how to swing a zweihander gets no help from that in the attack bonus department, but my ability to crack wise and be persuasive in the real world can often get me to be able to avoid actually having to roll no matter how fair and logical the DM is.

So focus on what you are trying to do...add some colour as much as you can. (bring up points, say you want to hint at an implication of X, give a hint at style (high class, harpy-ish, vampy, intimidating, cold, lawyer-y, etc.) and then let the dice say what you are doing.

over time you'll probably get a feel for the right mix of you actually using your voice and having the dice help.

[dragoeniex]

Okay, lv 5 - 20 bard and full time software support worker here with a few tips for getting people on your side.

1. Use "we" when speaking about someone's troubles, even if it's just on their end. "Is that right? How awful. There must be something we can think of to help." Verbally, you're positioning yourself as "on their side."

A bit harder to notice when you're traveling with a group that counts as another "we," but still handy. Especially in private asides.

2. Empathize and mirror back statements. "Oh, that does sound hard. I think that might drive me mad." or "How exciting! Why, how /did/ you accomplish that?"

People like to feel validated, and it also shows you're paying special attention.

3. Ask open-ended questions if you get stuck. "What are your thoughts so far?" "Is there anything else you'd recommend we look at here?" "I'm curious how you're feeling about all this."

It's a prompt for them to give you more to work with. Either better advice, or more clearly defined stances so you know how it's going so far.

4. Add some transparency in when possible. "I want to get my friends out of here, clearly. But then, everyone wants something. What about you?"

"I'm afraid I don't have an answer, but I do know where we can find one."

And so on. Some of these might be half-lies (like if you don't actually know where to get info but really need to buy the party time), and it still tends to lower people's guard. If you show a card or two, people are less likely to think you're out to con them. And if these are honest, they can help you not to panic over lying and keep calm.

5. Utilize your teammates! Does your ranger friend know how to track better than the bloodhounds of the gods? Introduce them to the angry noble looking for a vanished rival or lover. Talking to a group of cranky dwarves? Let your cranky dwarf lead this interaction- he speaks the language of gripe fluently! Political person usually only sees cases on bribes you can't afford? See if you can get info on a favorite food or two from staff or neighbors and have your supreme chef buddy cook up the most tantalizing gift.

You're not in this alone, after all. Others bring things you can't to the table, and thank goodness for that.

[Duff]

First off, you've picked a character outside your comfort zone. Respect!

If I've read your post correctly, you're in the sort of game where sktarq's excellent advice about letting the dice take care of technique wouldn't fit well. My advice is based on that, otherwise go with that unless/until you're happy you have the line you want.

Playing a character more articulate than yourself in that sort of game requires more suspension of disbelief to work. The GM (and if needed, other players) have to accept that your character is saying the right thing in the right way. So you say "Hi Sir Knight, can you bring your huge armour with us?" and the GM (assuming any needed social skill role succeeds) simply treats that as the best offer the bloke in armour has had all day. Ask if you can try again when you flub your lines in a way your character wouldn't. If you're GM will/can do that, it will help your social anxiety and that in turn will help you get into the character and work on your lines and your delivery.
If the group you're in won't/can't accommodate your skills, you probably need to pick a character a shorter distance from your comfort zone.

Some of the posts above give good advice about how to improve your ability to come up with and deliver the lines. Try them, find what helps you. I would especially recommend choosing a character to base their dialogue style off. Look for chances to use their lines and work on an ability to "Riff" on them and preparing a few lines.

There's 2 things you can get out of this, fun and improved social skills. If you aren't getting enough of them to justify the stress, put the character aside. Play them in a different group or save them for when you are more confident in that group. Write them into your novel

software support worker here with a few tips for getting people on your side.

OMG you sound like the call centre training manual I'm going to write one day! I can vouch for these as techniques that work in the real world.

How well they work in game is up to your GM

[ErdrickOfAliaha]

My tip: Erroll Flynn films. Most of the charm slides masculine, I mean these are 50's and 60's films, so take that into account. But as a typecast actor Errol does a great job showing off classic swashbuckling. Truly shining.

Have you read Cardinal Richleu (sp) or seen 3 musketeers? The classic swashbuckler is just an elder era version of James Bond: classy, witty, generally considered attractive etc.

You will be helped in no small part by developing your comedic timing. Being charming isn't always about saying charming things. Think about why you started dating your partner. Are they funny? Channel that kind of behavior, and you're well on your way to having Charisma work for You.

[dragoeniex]

OMG you sound like the call centre training manual I'm going to write one day! I can vouch for these as techniques that work in the real world.

How well they work in game is up to your GM

Haha, thank you! I will say these bits were written with roleplay in mind, as I try to stay away from charming half-lies on the phones, etc. But most of the concepts hold true.

That's true, regarding the outcome depending on the DM. But there's a nice self-fulfilling perk you can get going here too by using things you feel are reasonable and on the persuasive side. By feeling you're doing a good job, you start coming across more as someone who would do a good job, and that tone can get across quickly.

I do agree with your advice on, if having trouble, OP should try relaxing and letting rolls augment their attempts. It's a good thing to discuss with the DM in general when a player isn't sure how much rolls vs. wording weighs in.

[patchyman]

Haha! I am in a slightly similar situation having just rolled up a charming illusionist. One thing that has helped me is to observe and copy the people I know in real life that are charismatic. I just say to myself: what would X do in this situation?

Overall, I find “faking” this charisma to be easier in-game rather than in real life because I know I am doing it with friends.

A second bit of wisdom that I’ve learned from observing more charismatic people is that being charismatic is less about saying something witty than about being willing to put yourself in a position where a more introverted person would feel embarrassed. Real life charismatic people will talk to anyone, show interest in what people are saying, and be willing to ask questions and make polite requests.

Next time your party accepts a quest, just ask if the quest giver is willing to provide a guide, or a mule, or something to help out in the quest.

[False God]

It's not going to be particularly easy to play someone more eloquent and charismatic than you are. I think a useful tip to fake it though is try speaking less, but better. If you can't think of something charismatic to say, say nothing. Coming off as brooding is better than saying something dumb and coming off as a joke. Put your effort into making the lines you do speak better ones.

THIS.

This is also IMO, the correct answer for any high-mental stat character.

Speak less, but make what you do say more impactful. If you have nothing of value to add, say nothing. Charming characters can appear brooding. Smart characters can look studious. Wise characters can seem thoughtful.

Write yourself some ideas at home. Practice being "in character" in the bathroom mirror (seriously, it works). When you're comfortable, talk to yourself in character until you get a good feel on when they speak, and when they don't, and when they do, how they speak.

Also: SLOW DOWN. Unless your character is particularly hyperactive, one of the hallmarks of "good speech" is pacing yourself. Be it charismatic, wise, or intelligent.

[Tanarii]

Hire a lot of henchmen and mercenaries.

Man I miss the original Cha sometimes.

[Kaptin Keen]

This is for a dnd 5e game, but anyone skilled roleplayer should be able to help me out. I'll cut to the chase. I just started playing an aasimar swashbuckler rogue, who's meant to be a charming character (Expertise in Persuasion and Deception). However, oftentimes whenever I spoke in character, it was pretty stupid or not how I intended. Our campaign is a dark intrigue sort of game that is very roleplay and consequence heavy. (We speak in character via accents btw).
It's been giving me social anxiety.
What's your tips for roleplaying this challenging situation? Help a girl out!

You watch Stranger Things? Of course you do - everyone does.

Steve Harrington is awkward, clumsy, often stupid or at least slow on the uptake. He is also the characters 'charismatic' character. I'd talk to my GM, and explain that my character isn't the sort of charismatic you get in polished politician types - but the type of charismatic you see in a character like Steve.

And just let the rolls stand for themselves. Your high modifier means .. you are charismatic. It's not necessarily about having something good to say - it's just as good to say something silly, but saying it in a good way.

[Spore]

My advice. Talk to your DM about it. Much of the RP of a charismatic character depends on a positive reaction of your surroundings on them. Tell them you want to make this character pop and RP correctly but you struggle so. Ask if he can make "passive persuasion checks" for you and have his NPCs act accordingly.

I know when a particularly charismatic person enters interaction with me, generally all the charme becomes BEFORE the actual conversation. Of course being suave adds to the experience, but having people already gravitate towards the charismatic character definitely helps.

Also remember that "charisma" can have many faces. Your character can just be objectively hot and sexy. You can be verbose and just be a nice guy, that people like because he is nice. And you can be a suave sweettalker, but you don't have to be. Just because swashbucklers stereotypically are suave, yours does not have to be.

Also my DM and a fellow player RPed what I call "principled charisma" (yes I just invented that term). His characters do not talk much but his characters usually share a few traits.
- They are reliable. You can count on them, if they intimidate you, they can follow through on their threats. If they persuade you to allow helping them, they will help. If they use deception (which they almost never do) it is to manipulate people into risking less or allowing to be helped.
- They are usually doers instead of verbose talkers. They use simple language, short logical strings and do not try lawyery verbal acrobatics. Example: "I will save the king but if you add a bit of gold in beforehand, our job will be easier." instead of "We are risking our lives here. The least you can and should do is pay 50% upfront, as well as provide transportation to all of us, and knighthood to me. Oh, and you have to pardon any and all crimes linked to the king's rescue."
- Be aware of what 3.5 called cirumstantial boni/mali. You can't convince an evil cult leader not to incarcerate his virgin daughter to be sacrificed to the aboleth. You can however tell him you want to pledge yourself to the service of his dark master, because the king pays not much at all so you would love to see the kingdom fall (present notorious do-gooders ruin THAT bluff however).
- Generally avoid flashy combat tricks that would RP your cocky nature but could ruin your reputation. You don't HAVE to swing down on the chandelier if there is a perfectly servicable stairway. It is odd but once you're known as Athreus, the stupid swashbuckler that got almost crushed by a chandelier, no amount of sweetalking will ever be the same.

[Lorsa]

The advice from Spore is very good, just the one I was going to make myself.

Basically, try to get buy-in from your DM. We know that a character is charismatic based on the reactions of people around them. If NPCs respond in a way that assumes whatever you said just "happened to be the right thing", then your character will appear just as charismatic as you want.

Much of the problem with playing charismatic-type characters comes from being unused to it and thus overthinking everything. So let me ask you a question. In life, do people usually find you likeable and sociable? If so, then you have it in you and just need to act more natural. Basically, stop thinking about what to say and just say something. If you really struggle to be likeable in real life, then it is a bit harder, but many of the advice in this thread should help.

I'll add in another thing though: body language.

When you sit around the table, what is your usual posture? Rather than starting with changing the words, maybe you need to start by changing how you sit.

Basically, confidence creates charisma, so back straight, shoulders back and chest forward. Try to smile slightly at all times, especially with your eyes. If you want to project "I know what I'm talking about" tough leadership charisma, then put your hands together into the "V-shape" (thumbs meeting each other up and the other fingers meeting each other forward). If you want more nicer, slightly contemplative, fold your fingers together like many Christians do while praying (if you know what that looks like). For welcoming and inviting "I've got nothing to hide" gestures, show the inside of your palms by moving your hands to your sides. Lean forward when you want to show interest in what someone is saying (perhaps resting your chin on one of your hands). Lean backwards when you want to be relaxed, maybe even leaning to one side of the chair (try that, while smiling slightly, raising one eyebrow and saying "hey, how're you doing?" in a Joey from Friends imitation). Also, last but not least, AT ALL TIMES, keep your knees about a shoulder length apart. Don't overdo the spread, but from your legs should always have a distinct V-shape. You can place one foot on top of the other knee at times if you want, but don't do the standard "crossing legs" thing. Having a decent leg spread is imperative to project confidence and in turn charisma.

Hope that helps.

[darkrose50]

While charisma is not looks. Looks is charisma.

Being attractive is a large social advantage. They have done studies where they take attractive folks and via makeup and/or padding remove their attractive appearance. They are treated differently. The results are telling.

Your clothing is a large part of how you are interacted with. What you wear is important. I once had a boss that did not hire someone because he did not like his shoes.

Normally I want to blend in and not be noticed. Normal blue-jeans (or cargo shorts), a baseball camp (or a beanie), a solid color t-shirt without anything on it, and solid color black sneakers seem to work. My brother-in-law likes pointing out at GenCon every time someone wearing similar outfits walks past, and this is often. I look like my people (RPG geeks).

If I wanted to be noticed, then I could be by changing my cloths. It is quite something. When I was in my early 20's a group of friends and I were an extra in a university training film in downtown Chicago. We all dressed up, and I wore a suit. When we broke for lunch there was a man asking for donation for the poor. When we walked past him, he became very indignant and yelled at us "Not everyone is as fortunate as you!"

When I want to be left alone I can wear overalls, and then people give me wide birth. This is nice when I do not want to interact with store clerks asking me if I want to be helped with something.

Role-playing charisma could be as simple as others treating you well based on how attractive you are, and/or how well that you dress.

I might be a bit clothing blind, but it often would not matter what my significant other wore. She could have worn a potato sack or a simple black dress, and it would not have changed how attractive she was. People are strange.

[Lorsa]

I might be a bit clothing blind, but it often would not matter what my significant other wore. She could have worn a potato sack or a simple black dress, and it would not have changed how attractive she was. People are strange.

Clothing matters most on first impressions and less and less the more you know them. For someone you love dearly, your situation is hardly outside of the norm (in fact, I think many people feel the same). The question is, if it was the first time you met her, would you have found her equally attractive in a potato sack or a black dress?

[Hand_of_Vecna]

In these situations the first step is to be open with your DM and possibly the whole group and tell them that you are trying to play a certain type of character and that you would appreciate your in character words being viewed through that lense.

Fast talk, persuasian, bluff, etc. usually involves not just coming out and saying what you want.

Someone actually very skilled at these things may sometimes find themselves using the skill on the DM rather than expressing their will to use the skill.

Someone skilled at roleplaying these skills will often manage to communicate to the DM and other players what technique of convincing they wish to use and what skill they want to roll.

Not falling into either camp you may have to hybridize narration and roleplay. Several people in this thread have detailed good techniques of persuasion, but just studying those on paper won't make your performance good especially not when you suffer from social anxiety. Try to use these techniques, but periodically break character to tell the table what your character is doing.

Say You've been pulled over by the police for an illegal turn. Sorry I'm on mobile so I'll be using parentheses instead of italics.

"I must have missed the sign (I say to acknowledge their interpretation and authority) I'm just leaving an appointment at the VA hospital and thought I was ok to drive (at least in most parts of the United States there is a level of comraderie between Police and Military/veterans and their families, a character with the right skills could easily fake this association especially being a child or spouse having a sticker on the car would be helpful in this scenario so you don't come off as a whiny kid demanding privleages for your father's status) I should have let the wife drive. (What you mean to imply here differs based on the gender and other observations you've made of the officer. With a male officer you may be presenting a chauvenist persona of a man who would only allow his wife to drive under the most dire circumstances. With a female officer you may instead be meaning to play a typical sitcom husband who knows better than to have not asked his wife to drive. This is also a great place for the "spouse" to chime in with an aid another.)

The best part of this technique is that over time the DM will learn your presentation of your character and need less explanation of your intentions when you speak on character.

[darkrose50]

Clothing matters most on first impressions and less and less the more you know them.

This is true. If we are discussing NPC's, then most rolls are made to convince NPC's that are not well-known. I can see the princess or prince needing to make a roll to convince their father or mother into some political decision, or perhaps even for getting out of being grounded.

For someone you love dearly, your situation is hardly outside of the norm (in fact, I think many people feel the same). The question is, if it was the first time you met her, would you have found her equally attractive in a potato sack or a black dress?

I really think that I am clothing blind. I like dresses or skirts, because legs. I prefer hair worn up, because necks. A black dress and an inexpensive swimsuit both knocked my socks off.

I would not have been attracted to a girl based on the brand or the price of her clothing. It never even came close to entering my mind. Hormones in young men are quite something. I might not immediately notice a girl who covered-up in bulky clothing, but eventually, there would be gym or swimming and that would render that point moot.

[Evil DM Mark3]

Charisma is the most badly treated stat in DnD. With every other thing state intentions, roll dice and describe results. With charisma we describe results, maybe forget the dice and never explain intentions.

What do I mean?

With Dex : Rogue : I try and switch the books without him feeling them move.
DM : Roll Dex with disadvantage
Rogue : 21 and 19.
DM : You manage to time the swap for the peak of his breathing cycle, the books swap out in the instant his hand is off it.

It lets your character's training and skill shine and doesn't make you have to handle every detail of two fictional events (the one in your mind and the similar but different one in the DM's mind)

With Charisma: Rogue : I lie and tell him that we are here to perform a surprise audit.
DM : He says they don't have surprise audits.

OR

Bard : I sing a raunchy song about pirates
DM : Roll Performance
Bard : 8
DM : You do it badly.

The problem is that we have a lot more investment in what our characters say and do, so often we won't accept the same level of insolvent as we would for other rolls. At my table you can be as descriptive as you like, but if all you want to say is "Sorry, can't think of anything, I roll Bluff to convince him we should be there" then that's fine.

[redwizard007]

There is tons of great advice here already. The bit I wanted to add is from personal experience. I've always felt like an introvert. Hate speaking in front of people. Solos in anything are terrifying. Entering new social environments is a cause for lost sleep.

And yet

I've had major roles in multiple school plays, had dozens of solos or small group appearances with choirs, always gravitate towards leadership roles, can chat up 90% of the patrons of any particular bar regardless of gender, and have been incredibly successful as a regional sales manager where I am constantly developing new relationships.

How do I pull this off?

Acting. Seriously. I get in the mind set that I am someone good at these things. Start easy, like putting on a role at th he has station or convenience store. Nothing elaborate, just a more confident version of yourself. Think you-but-famous (or rich, or as a superhero.) Paste a big smile across your face and stroll in like you own the place. Don't nod at other customers, ask how they are doing. Make idle chatter with the clerk for a minute while you cash out. Now scale this up to other interactions in your life.

Your character is no different. He's not you. He doesn't have your insecurities, just your strengths. Take that same attitude you have in the store and apply it to your character.

[Psyren]

Roll and describe what you want to do, then ask the other players to help you roleplay/act it out. Not being charismatic IRL should never be a barrier to playing a charismatic character, the whole point of roleplaying games is to be something you may not necessarily be in real life. Someone at the table (including the GM) who can think of something clever to fit your roll will be happy to help usually.

[Tanarii]

Charisma is the most badly treated stat in DnD. With every other thing state intentions, roll dice and describe results. With charisma we describe results, maybe forget the dice and never explain intentions.

Depends on the edition. For example 5e DMG gives remarkably clear guidance on what kinds of things charisma checks can accomplish, and setting the DC.

Of course, the entire basis of 5e is the DM is supposed to, for all checks, first consider if a dice roll is even needed. So for all checks, including charisma, its supposed to be: state intentions, DM decides if dice are needed, roll dice if applicable, describe results.

The vast majority of RPGs follow that same flow, and many (most?) Caution the DM not to roll dice unless there is a question of uncertainty. Somehow in D&D 3e (earlier?) it became standard to think dice were always rolled, and that "roleplaying" (not really but often called that) to bypass charisma checks was an outlier.

[kyoryu]

To use terms from Burning Wheel, I find it best to consider both the Intent and Task:

Intent: What are you trying to accomplish? If you do good at this, what happens?
Task: How are you going to accomplish this?

If that's all reasoanble, then roll the dice. How well you narrate or speak shouldn't be the sole determinant, though (depending on table preference) it may give some amount of bonus.

[Duff]

Think about the role of smalltalk at your table.
Will it work better for you playing your character if you play it out with the GM. Speak in character "Hi Sir knight, how was your trip here?"
Or not. out of character to the GM "I do the polite small talk and then I get to the business - "Sir knight we need you to..."

If the dynamic is right, the small talk will give you and the GM time to get into character with some easy warm-up banter and it's fun. It sounds like the sort of group where that can be fun.
If it's not right for that, the small talk may just be awkward and boring.


Also - be outrageous at least sometimes. Use classic so-cheesy-it's-good lines with comic exaggeration of facial expressions. Get the group laughing while you're centre stage. It's easier to feel (and act) charismatic when you are the center of positive attention

[jayem]

Acting. Seriously. I get in the mind set that I am someone good at these things.

Your character is no different. He's not you. He doesn't have your insecurities, just your strengths. Take that same attitude you have in the store and apply it to your character.

DnD is a game which gives some other advantages. Your character not only has your strengths but his strengths
The charismatic because other people know they should find you charismatic effect is built in.
The externalities is built in, you can show off your +5 sword, introduce them to the Queen. You can deliver on your promises.
It's a game, all the bits of psychopathic-charisma apply. The NPC's literally are there for you to play with (if you leave them destitute, broken hearted and insane, no harm is done). Ultimately you will escape consequences (your character might have to roll against their vengeful relative and die, in which case you restart, who cares. Or if you show real life contempt, don't do that.) so you can take a risk.

[TakeitVillain]

My tip: Erroll Flynn films. Most of the charm slides masculine, I mean these are 50's and 60's films, so take that into account. But as a typecast actor Errol does a great job showing off classic swashbuckling. Truly shining.

Have you read Cardinal Richleu (sp) or seen 3 musketeers? The classic swashbuckler is just an elder era version of James Bond: classy, witty, generally considered attractive etc.

You will be helped in no small part by developing your comedic timing. Being charming isn't always about saying charming things. Think about why you started dating your partner. Are they funny? Channel that kind of behavior, and you're well on your way to having Charisma work for You.

Thank you so much! Reading three musketeers is now my top priority lol.

[Tawmis]

This is for a dnd 5e game, but anyone skilled roleplayer should be able to help me out. I'll cut to the chase. I just started playing an aasimar swashbuckler rogue, who's meant to be a charming character (Expertise in Persuasion and Deception). However, oftentimes whenever I spoke in character, it was pretty stupid or not how I intended. Our campaign is a dark intrigue sort of game that is very roleplay and consequence heavy. (We speak in character via accents btw).
It's been giving me social anxiety.
What's your tips for roleplaying this challenging situation? Help a girl out!

The easiest thing is - put yourself into the shoes of someone YOU find charismatic in real life (whether a real person, or a fictional character from a movie or book).

Imagine yourself as that person - how did they speak? How did they act?

For example, many find Doc Holliday (Val Kilmer in Tombstone) very charismatic. He was suave, confident, even as he was dying.
Danny Ocean from Ocean's 11 was very charismatic also. You also had James Bond.

And there's different kinds of "Charisma" that you can try to pull off.

Here's a list (sorry they're all male, just googled charismatic characters)...
https://effortlessgent.com/7-classic-movie-characters/

Might help maybe have you step into their shadow as your character to help define what type of character you want to try and be.

[Faily]

I always try to think of how my character is charismatic.

Are they just naturally sweet and innocent? (think most female characters in shows for younger audiences)
Are they savvy and smooth? (think James Bond)
Are they dangerous and persuasive? (think Loki in MCU)
Are they just goofy and friendly? (think Joey in Friends)

The above advice of basing it off of a source you are already familiar with is a very good advice. It's easier to mimic a charisma and think of what to do/say when you can ask yourself "what would James Bond do/say in this situation?".

What you can also do is to think more about what *your* character would do outside of game time. Think of hypothetical scenarios, or insert them into scenes from tv, movies, and books. Ask yourself "how would my character act in this scenario", and try to work from there.

[Mordaedil]

A thing that cracked it for me is that realization that charisma in a game isn't charisma, it's more a factor of what you can get away with.

Be absurd, ask for things beyond the pale. Got caught red-handed in the middle of a crime, pull the guard aside and start to put together a story of what is happening before him. You're not thieves, you are working undercover to arrest a group of thieves and he just came at the wrong moment and needs to act along to allow you to move on. Or it is his ass that has to answer to the captain.

For more fun, try to use persuasion as a weapon in combat.

[Psyren]

A thing that cracked it for me is that realization that charisma in a game isn't charisma, it's more a factor of what you can get away with.

Be absurd, ask for things beyond the pale. Got caught red-handed in the middle of a crime, pull the guard aside and start to put together a story of what is happening before him. You're not thieves, you are working undercover to arrest a group of thieves and he just came at the wrong moment and needs to act along to allow you to move on. Or it is his ass that has to answer to the captain.

For more fun, try to use persuasion as a weapon in combat.

The initial approach here is sound - figure out your objective (e.g. we need the guard to leave without sounding the alarm) and then figure out a way your fast-talking character would achieve that objective, crowdsourcing ideas OOC if needed. "We're contractors upgrading the security here" or "we're extra security, we received word this room would be targeted and so we're moving the valuables somewhere more secure." - or "we're investigating the crime scene in order to catch the real thieves" aren't bad options for a heroic PC.

I'd be wary of being too outlandish however - this can invoke circumstance penalties, higher DCs, disadvantage, and/or outright failure depending on system. The best bluffs have a grain of truth, enough to be plausible, much like the best lies.