As a DM, I’m not asking you to act, I’m not asking you to engage in improvisational theater, I’m asking your approach. I mean, I’m a “fade to black” DM when it comes to spicy roleplay, so I probably wouldn’t for the named situation in this meme, but let’s say it’s somehow relevant beyond the laughs of “horny bard”. Are you being cheesy and trying to get the bartender to laugh? Are you trying to be suave? Are you just socially indicating interest and letting the bartender decide what they think of that? These matter for what kind of reaction will come about from either a success or a failure on the roll, and it’s not my job as a DM to decide for you what approach is best for the situation… determining the approahh ch is the game. You can tell me your approach via ACTING! or just by describing it, but I really need to know what your character is doing.

But really, don’t worry about your own charisma. You don’t need to be suave or charming if your character is. I just need to know what they’re trying to do, not see you do it.

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.