Gallus (RD): So how do I get out of here?
DM: Basically, Gallus, I'm going to have you roll Acrobatics a bunch of times, because the trick is to cross the right beams and not accidentally cross the wrong beams. Successes cancel out failures, and vice versa. Crossing a beam makes it disappear. It may take a little bit, so could someone watch Gallus's rolls for me?
Ocellus (TS): Uh, I can.
DM: Great. DC starts at 14. Every 10 attempts lowers the DC by 2. Let me know if you reach a net of 7 successes, 6 failures, or 30 attempts.
Gallus (RD): Okay… <roll>…
DM: Meanwhile, Smolder…
Smolder (RT): Hm? Back to me?
Gallus (RD): <roll>… <roll>… <roll>…
DM: You find yourself in a dragon's worst nightmare: A crystal dining room where two bedazzling mares are having a tea party.
Stepford Mare 2: And I told her she was the CUTEST pony of ALL ponies!
Stepford Mare 1: Oh. My. Gosh! What did you do after that?
Stepford Mare 2: We talked about dresses and makeup for literal HOURS.
Sandbar (AJ): At least it's something you've got experience in.
Smolder (RT): As Rarity, under normal circumstances, maybe. But for a change, I'm playing as a young dragoness of noble bloodline who sees decorum as a farce and only values strength. So in this new bruiser mindset, I'm finding this to be… genuinely… powerfully revolting. Is this what it's always looked like from the outside?
Gallus (RD): The first few times? <roll> Yeah.
I love me some guile characters and veiled casual conversation for the sake of probing for information, but boy does that playstyle have its challenges. Sometimes your only consolation is the twin daggers your character has holstered beneath their tailored clothing, or all the arcane might just a few words or gestures away.
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I think I've grown into flexile characters a lot. I tend to have a character that fits very nicely into several of the basic party rolls, and can do them pretty well. I either tend to lead by example or aid others to doing what they do, but better. Favorite archetype is the older campaigner that's leading this group of newbies around so they don't die, then eventually garnering respect for them as they "prove themselves". I do my best to not make that as overbearing as that sounds. XD
That sounds dangerously close to the guy that is the same level as everyone else, but still says, "Not bad, for a beginner" every time someone else accomplishes something. A.K.A. the character all the other players want dead. :p
It probably is. That's actually a really bad habit of mine, picking archetypes that are really super easy to fuck up, and would piss others off if I did. It's never a conscious effort, but when I really think back...I've done it a lot. Luckily, I'm always invited into the next game, so I HOPE I'm doing it right.
Just to change things up, you should try the Wide-Eyed newbie who lucks into the right decisions sometimes. It can be fun to just have your character be really enthusiastic about the whole adventuring thing.
Speaking of flexile, I tried making a scholar/techie character for an upcoming oneshot, but our GM kept suggesting a certain combat class ("Background"), which implies it'll be needed. That said, he's still got enough scholar (in this case: lore, medic, and crafting) chops to fit in anywhere - which, combined with said combat specialty's focus on punching, lets me unapologetically use a certain theme that goes with everything.
The first time I tried out D&D 5e I played a half-ork barbarian with a pretty decent charisma score. She wasn't the party face, but she sure tried to fit into various upper societies to try and learn information (or to just not get the party into trouble). It was a lot of fun playing a brute that was attempting to not punch all her problems, and failing Charisma checks was often more fun and interesting than succeeding. XD
Interestingly, getting folks into trying new rolls and types is often being a foil to them so that they can be true to their idea, but also be a point that you aren't.
Our 5e kobold thief is an infinitely better mechanical diplomat than my 5e bird wizard. But at the same time, we have usually vastly vastly different dc's for our diplomacy.
He is playing true to kobolds, snarky, sometimes cruel, or cold, but he tells it like it is. He is the bad cop of diplomacy. He will insult you, belittle you, and 'he's not wrong or untruthful' through it all.
And everyone in our party has the moments we are very much opposites in social situations. The bird will be the foil to the dragonborn, our human to the bird even.
Everyone is together in how we play, but we each stand aligned apart, and respected for it.
The most difficult part of playing a guilefull character is when you have a DM who... isn't. You try and do the classic "I'll scratch your back if you scratch mine" and they have the NPC Mob Boss go "I've got scratching posts, honey. Cash. Now."
When the worst fear the GM put is... Something they liked to do with a previous character in the past. Any good story like that? As the GM let you take a look at the things someone liked in the past only to be shamed thinking "how could I liked this?"
Reminds me of a character I played in post-apocalyptic game. He was just called 'the Chairman' and he was an amoral snake that could talk his way out of anything. In a game where character death is commonplace he was the only one to survive to the end of the campaign. It helped that he wasn't particularly greedy or hateful. He just wanted to run his business and only caused trouble for people looking to interfere with it.