The Assassins meet

[Gilimallow]

So I've been making a dungeon for a while. This is one encounter that I came up with, that I am pretty proud of. So we have this one character, he is a rogue level 2, and assassin level 1. He is lawful evil, which the rest of his party really didn't like much, they thought he would back stab them, but I am pretty sure he wont. Anyways, I am going to have them walking down a dungeon hallway, when suddenly, an assassin approaches from behind, and invites the player I was talking about to join him, and take over the world. I want to see how he reacts to this. This is also a way for him to get some special loot. I am going to have him drop leather armor, a cloak of elven kind, and an assassin's dagger. So what do you think about?

 

[Stormonu]

"I don't know you, you don't know me. But clearly I can trust you and your friends. Have some free, powerful magic items without question of acceptance."

"You may now proceed to kill me and keep the loot."

Unless the approaching assassin is a native of the "dungeon", I don't see why he is approaching the party member in the open - and certainly not in this place. A true assassin will have been watching the character for some time and likely approach the PC when alone (and defenseless, should things go south). Likewise, I can't see the NPC giving the PC anything until after the PC proves themselves dedicated to whatever cause the NPC assassin has likewise dedicated himself, possibly even proving his "loyalty" by turning on his friends and showing the NPC assassin that the PC's loyalty to the NPC is greater than to the rest of the group. Unless the "drop" your talking about is the actual treasure the PC gets for defeating the NPC assassin.

A better scenario might be that the NPC assassin has been sent to kill the PC assassin by someone else the PC has offended or who thinks the PC threatens his position. Or perhaps the PC assassin is to be given a choice - join the brotherhood, or die.

 

[Rechan]

A better scenario might be that the NPC assassin has been sent to kill the PC assassin by someone else the PC has offended or who thinks the PC threatens his position. Or perhaps the PC assassin is to be given a choice - join the brotherhood, or die.

Or the PCs find the body of the dead assassin, with the assassination orders on his body. He's been sent to kill someone in the dungeon, so when the PCs kill the mark (since adventurers generally kill anything in the dungeon anyways), they could try to claim the reward. At which point it would introduce the assassin PC to the guild, allowing him to join up/get missions.

Or the assassin is actually following the PCs. Not because he wants to attack them, but because he has a target in the dungeon, but doesn't want to have to deal with all the dungeon denizens. He lets the PCs plow their way through the dungeon, setting off all the traps/killing the indigenous lifeforms, and he sneaks in behind them into the secret door leading to the lair of his target. But the PCs come across him.

Or hey, he could even be in then dungeon, trapped somehow, and offers the PCs treasure in order to help him, and in the process he recognizes the potential of the PC.