Jester is a Tag in Divinity: Original Sin 2 that allows the player to have certain dialogue with NPCs and certain options during Quests. Please see below for a list.
Jester Dialogue Options
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I managed to convince a bear in nameless isle to let it all out and make it happy with the jester responses.
First time the jester tag actually helped someone instead of mediocre jokes or getting someone at my throat.
One of Griff's thugs in Fort Joy will ask you about the crate of stolen supplies and you can tell her to "have a crate day". This will result in her letting you off the hook and trying not to smile when she talks to you. It's not very important but it made me happy.
0/10; Does not work with undead race to provide constant skeleton puns in conversation
Jester tag seems to retain its useful when speaking with adolescent NPCs, usually amusing them or lower their guard enough to trust your character more. Besides that it appears to offend everyone else in the game.
I only found this Tag useful when playing as a villian, most of the characters you interact with seem to get upset by your jokes or inform you that it is the wrong time to be saying such things. When playing as the villian this seems to fit better, side note, i dont think there was ever a time where the jester tag actually solved or made any quests easier. Get scholar if you want that.
Most useless tag in a game, not a single joke in whole game was even a bit funny, this tag set your character to*****ty comedian with bad sense of humour. I guess larian just trolling players for getting this tag or this is really bad writing..