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Of course there would be a skill challenge...
This waitress is called Waltz, and I made a token of her to play in a one-shot:
ShowWait wait wait OP, I smell a paradox here. Hasn't the little goblin sent her friends to scout the tavern ? How come this is a surprise ?
that's a good question. Is she surprised? She doesn't seem to be panicking...
I'm not sure Konsi has a nasty bone in her body.
The one she's using as a hair ornament is a dragon bone though.
I mean, me being the buff paladin I would be obliterated by this
Because they orc hasn't!
Razira is surprised, Konsi isn't.
It seems to me like Konsi set her up, and I'm here to see why!
If it were me, Id sing and make them regret putting me on the spot.
They said to perform. Not to be good.
I love this as an idea to try and get quiet PCs to possibly interact more.
Maybe have the party dip into an open door while they’re running from a threat or while trying to sneakily navigate the town.
Other things that work great for getting PCs to interact more with each other and story beats:
Have a plot where the characters either need to go undercover to scope something out, go underground to avoid attention, or infiltrate an organization - and they join a circus or a theater troupe, or similar organization.
Have a gift-giving ceremony or similar, that acts like a secret santa, where each character has to do something for the next in a circle.
Have NPCs take direct interest in one specific character and want to talk to them, not have another speak for them. Maybe it's a romantic interest, maybe it's a business interest. Maybe they own a store and think that one "hero" would make a great spokesperson "hello I'm shepard and this is my favourite store on the space station"
Have a newspaper/journalist want to interview a specific character about their adventures, or an author want to write the story of the group and interview them all.
Have an NPC in that PCs organization task them with organizing something or solving some problem, and directing the rest of the party to help "hey, our temple has a corruption plot, you're good at solving problems and rooting stuff out, could you start investigating?"
Have someone the party rescued or helped out start hero-worshiping a specific character, and want to become their squire or apprentice.