Why D&D?

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I literally already addressed exactly that.
Sorry, I must have missed something because it seemed you were saying that a short-term swindle, which was discovered later, would be a failure, and it wasn’t clear how that would be treated differently from the case where the mark simply doesn’t bite. But I take what you write below to be a clarification of the process.

Understand, the reason why a pitch works is because it is communicating relevant information. The prospect might see no need for an umbrella on a sunny day. So initially, he's not interested in buying one from you. If you pitch seemingly credible information that it will in fact rain today, that would likely lead to the prospect re-evaluating whether or not he wants an umbrella. If he wants one, now that he knows it will rain, he may buy one from you. If 15 minutes later he learns from someone else that, no, it's nothing but sunny skies ahead, he may suddenly feel buying that umbrella was no longer a good decision.
Yes, this covers one of the cases I had in mind, where the guy basically convinced me that I was getting the best deal possible, with something valuable thrown in. Arguably it applies to the other situation I had in mind.

I’m struggling to see how it handles a case where someone gets his way by sheer persistence and wearing you down. Or, again, seduction. I mean that in real life people are persuaded to do things about which they have misgivings, because their judgement is clouded by social hangups (not wanting to be rude), lust, etc. How do you reproduce that for PCs?
 
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I’m struggling to see how it handles a case where someone gets his way by sheer persistence and wearing you down. Or, again, seduction. I mean that in real life people are persuaded to do things about which they have misgivings, because their judgement is clouded by social hangups (not wanting to be rude), lust, etc. How do you reproduce that for PCs?

I think social hangups are easy to handle. If we're talking about an NPC with social hangups, what a PC needs to successfully persuade the NPC to action is first, discover that social hangups is the real motive that's making the NPC hesitate. And this can be a very difficult task in itself. People with social hangups often fire out a series of excuses that can act as a barrage of red herrings for the PC persuader seeking to find the NPC's motives. But once you figure it out, then the next task is to figure out a solution.

So what if a PC has a social hangup? It's just like the poker example. You have to leave it to the player to role play it. And accept that some players may just refuse to. But bear in mind, the player who never folds in a game of poker, while he does indeed completely hamstring any bluff skill the other players might have, is also not cutting his losses when the cards just aren't in his favor. You can still play that way, but no special rules or mechanics are needed to discourage it, because at the end of the day it's not a good strategy. And I would make the same argument for PCs with social hangups. Feeling the absolute freedom to be rude to other characters in the game is something rife with enough negative consequences that there's no need to head this off with special rules.

Lust is a little trickier because it's a lot harder to imagine circumstances where not giving into lust will come back to haunt you. It actually is a good strategy to never give into lust. That's probably why it made the short list of mortal sins. So what do you do about it? Depends how you want to run your game.

Back in the early to mid 90's when Aaron Spelling dramas were all over the prime time airwaves, I had this idea as a goof to make the Aaron Spelling roleplaying system. Because his shows kind of reminded me of the RPGs of the day. During this period, D&D had many different game worlds in publication, and so even homebrewed campaigns tended to be such that players had to make a bunch of new characters every time because the old characters weren't appropriate for the new campaign. Anyway, my satirical sense of Aaron Spelling shows is that it was only a matter of time before all the characters in the show slept with each other. So I figured, the Aaron Spelling roleplaying system would use Sexperience Points to advance your characters (it sure as hell worked for Brian Austin Green's character). Now I think it's a goofy solution for a goofy idea of a game I've had, but I'm pretty sure there have been RPGs not intended to be goofy that did something similar.

What I actually do in my campaigns? A few of things. First, I've always emphasized the mortality of PCs as a means of making procreation more desirable. No, there's no on-screen sex. But running the game world with the scope in mind of some day playing the child of your original character. You have to start at 1st level, but with a bunch of inherited magic items. Not a bad deal. And the different lifespans of the different races suddenly become really relevant, too. It's not the same thing as giving into lust at all, but it does mean "never have sex" is not a very viable strategy in my campaign. (Vows of celibacy and chastity of some religious orders are suddenly serious things.)

Second is similar to sexperience points, only less mechanical. Since I run a mythic-styled campaign, it's actually thematically correct that I pair up those natural desires which characters most likely have (like desire for sex or romance) with something of more tangible value that the player can appreciate. So it's not just that the knight rescues the princess from the dragon to win her love. It's that the knight is highly capable but doesn't know the dragon's weakness. He tries to rescue the princess but learns she can't escape unless he confronts the dragon, and she--having been held captive by the dragon--has been able to observe the dragon up close and has learned the dragon's weakness, knowledge she can impart on the knight. So only in their union do they have the power to triumph. A player might not be motivated by the Gwaelin's Love per se, but that it has the power to orient you in the wilderness can come in handy.

Third is not a common thing. But when I play Lejendary Adventure, the game does have Knacks and Quirks (sort of like advantages and disadvantages). Some of the quirks include extreme personality traits. Like Vamping/Womanizing makes the Avatar 90% likely to attempt to "dally" with one of the opposite sex just met, in general regardless of age or appearance, despite possible demands elsewhere. It's understood that this is an extreme personality trait, and for that, the player will have to submit to mechanics controlling his character. Magical charms and curses can likewise over-ride player will. A succubus flat out comes armed with the ability to Charm Person if need be. So I don't need players to voluntarily give in to lust for a succubus to work.
 
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