this post was submitted on 18 Jun 2025
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Ignoring the actual rules and mechanics is basically step one in almost every "isn't this goofy" D&D anecdote.
Not only is it not "decent damage" (even the buff it got in 5.5 just brings it from "the worst" to "poor"), it's also not a subtle thing you can just drop on someone unsuspectingly.
Spellcasting for an attack is an obvious aggressive action, which means an initiative roll comes first to see if you even manage to get it off before they clock you. It's also not like everyone around just shrugs and lets you go about your business because all you did was hurl an insult. You attacked someone with an offensive spell, the response is exactly the same as if you threw a firebolt at them
The flavor of insulting someone to death is fun, I'll grant that, but there's nothing special about Vicious Mockery mechanically that makes it immune to initiative order or people noticing what you're doing.
"You unleash a string of insults laced with subtle enchantments at a creature you can see within range."
...its only component is verbal, and while it's not subtle casting it's fair to characterise as subtle casting; i'd argue for first-round surprise in the context of open dialog and in fact that's how we've played it at my tables...
I'm okay with a DM ruling that it's possible to cast it in such a way that someone is taken off guard, sure. Maybe a performance or deception vs hostile creature(s) insight rather than the typical stealth vs perception when determining surprise from sneaking, which is not RAW, but I think sounds reasonable. I'd definitely not consider it to be an automatic aspect of the spell at any table I ran.
And you absolutely could not avoid a fight and just walk away from the situation with plausible deniability because you "only insulted them".