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When making some sort of Persuasion roll against an NPC, it's common to offer dice bonuses/penalties for roleplaying the conversation in a convincing/unconvincing manner. (Maybe it's a good thing that Jim is here dealing with a PC played by Sally, rather than an NPC.)
When you think about it, this is slightly odd. You don't give PCs combat bonuses/penalties for being able to do karate in real life, or Stamina bonuses/penalties based on their ability to do a 5k run in the middle of the game.
Or at least most GMs don't. Maybe you should! At the very least you give your players an incentive get fit!
Commentary by Keybounce (who has not seen the movie)
Sorry Poe, that's not how you sell it. You have to be able to convince Kylo that you are not lying. You kind of failed on this one.
Sally is familiar with The Princess Bride. Of course, that assumes that The Princess Bride exists in this universe. In any event, Sally appears to be thinking it over. However, if a player wanted to work with another player, they would just say yes. If Sally wants to give the impression of being a hard-nosed (assuming that she has a nose) leader, she might do exactly what she did here, and say yes in the morning. Or, she might actually decide to kill him in the morning, because he did not sell the proposal. She has no reason to trust him, and certainly no reason to let him leave.
So, I would almost say that we have another player about to die. On the other hand, Kylo needs the information that currently either exists in Poe or in nobody. So Poe might be kept as a "He better have this information in there somewhere". Maybe Kylo will give him over to the scientists. Let them do experiments to try to recover the information that he's pretending to not have. Maybe Kylo will give him over to the torturers. Maybe Kylo will do the torturing.
I don't think Kylo knows about the droid. I think BB-8 has been unseen so far. If so, then the map data has a chance to get away, and the Resistance has their plot hook.
Episode IV, or V? Which path will things go down from here?
Commentary by memnarch (who has not seen the movie)
That's a really good point Poe. Vader basically had to wear that suit because health reasons, and Kylo looks like they're trying to be Vader 2.0 what with the black everything outfit and a red lightsaber. We'll probably never end up seeing what they actually look like until the end of the Episode (or the end of Episode IX), but I'd give it good odds that their skin is just as pasty white as Vader's was along with a few facial injuries which could include a missing nose.
Hmmm. That is, of course, assuming that Kylo is a living being and not a robot impersonating one. Sally was the one who ran the Robot Utopia campaign after all, and she's played the most robot characters out of the group so far. A robot being able to use Force powers would be a pretty big twist though. I'll have to keep this in mind for thinking more about later.
As for getting inside the Resistance and finding things out, Poe, the whole reason you went to Tatooine in the first place was to find things out because this was a secret mission and Leia is looking for information. You probably forgot that already, but this could work out in your favor of living longer and trying to make more money off of both sides again. And Kylo's not immediately chopping your torso open, so you'll probably live through the next session if you don't do something rash. Wait. Poe's being played by Jim. Never mind then.
...
I wonder if that phrase ever came up in the game with the darned persistent bad guy?
Transcript
Poe: Here’s the deal. You pretend to capture me, so you can brief me or whatever, then let me escape.
Poe: I’ll get inside the Resistance command structure, find out what they know about Luke and Achoo, and feed it back to you.
Kylo Ren: What if you’re lying to me?
Poe: I report to the Resistance that you’re an idiot. But then they know that already. No skin off your nose.
Poe: Assuming you have a nose under there.
Trooper Mike: Want us to arrange something special, boss? Polish one of my pieces? Orchestrate a blaster to his head?
Kylo Ren: Nooo... Take him away!
Kylo Ren: Good work, Poe. Sleep well. I’ll most likely kill you in the morning.
Poe: {being dragged away} So I got the job?!