As a DM, there are two reasons I ask this kind of question.
If it’s a player that I know is comfortable playing their role, then I am trying to get them to lean into the scene to assist with story pacing, or potentially to reveal additional information.
There are still benefits to asking it though, even if a player is not comfortable playing out the scene. Even without a spotlighted stage, you can still obtain a lot of character development by asking for additional clarity. For instance, did the character want to use a cheesy pickup line, or maybe a humorous anecdote, maybe they want to be really suave.
I would probably ask some leading questions like the above, but that additional info can still greatly expand the scene without turning it into a night at the improv.
Yeah, this precisely. I don’t expect players with Barbarians that have 20 strength to bench 400 lbs, so it’s fine if players aren’t as suave as their Bard, unless they want to lean into roleplay dialogue. It’s usually more than enough for them to say, “I try to charm the blacksmith by complimenting how nice a shop they have” or something like that and let the dice determine how effective they actually are at that.
