Roleplaying dilemma - what would you do?

[StreamOfTheSky]

You're not up on noncore spells, but you're using a PH2 class, the beguiler. PH2 has the Overwhelm spell at level 6, that is probably the simplest way to go about neutralizing him nonlethally, though there's definitely other ways if you want to use a lower level spell, I'm sure.

 

[Dandu]

Tenticoo wape.

Tell him to surrender when he's had enough.

 

[Persiflage]

Effective tactics (at least, the non-lethal kind) depend on the other guy's movement capability. If he has some sort of teleport, it's really, really hard to stop him getting away without just killing him outright. If he hasn't, it's really, really easy. Personally, I think Dandu has it right; tentacle-tastic tactics are the way to go. I'd modify the plan slightly though, as I wouldn't trust any offer of surrender. It's impossible for you to drop him straight to -10 with the damage as the tentacles only do 1d6+4 per round (unless you've modified the spell in some way) so you can just dismiss the tentacular goodness the second he falls unconscious, then have the cleric stabilise him. That beats accepting surrender from a self-confessed evil lunatic, six ways from Sunday.

On a related note, I'm surprised to hear you say he can't get away. His grapple check might not be worth a damn, but doesn't this uber-sneak have a useful Escape Artist score? I sure as hell would if it were my character...

 

[Dandu]

If he is a Necromancer, his devotion to wizardly studies will leave little time for such things.

If he is a Rogue/Assassin/Something like that, possibly... but I was unsure if Assassin was his occupation/title and Necromancer his class, or if he was some sort of odd multiclass.

If he is multclassed, just lob a Stinking Cloud at him before the tenticoo wape. And make sure to have a Silence effect up around him so he can't cast spells easily.

 

[Persiflage]

I was sort of working on the basis that if he was any kind of useful Necromancer, the OP would be dead already

Stinking Cloud is good. Lob in Kelgore's Grave Mist and Death's Call for exhaustion winsauce if you'd like the irony of using necromany spells against him. I'm assuming that you've got some way of spontaneously quickening spells

 

[radmod]

On a related note, I'm surprised to hear you say he can't get away. His grapple check might not be worth a damn, but doesn't this uber-sneak have a useful Escape Artist score? I sure as hell would if it were my character...

First let me say that I'm likely giving a wrong impression. While I call him a necro-assassin it's because that's his attitude; I don't know exactly what he is. He is a 2e transitioned into 3.5, and has a few cleric levels of some sort mixed with some other 'sneaky' levels. Further, I seem to recall he said his Drow race was +3 ECL so that leaves him with 9/10 HD. He's the type of guy who would spent mucho points in Hide, Move Sil., Disguise, Bluff, etc. so I doubt he had much left for Escape.
Since Evard's grapple is CL + 8, that means the tentacles are +25. His grapple (with a penalty in STR) is +6, so I always win. Even with the average 7.5 dam, that means in the 16 rounds he would take 120 hp damage.
However, you make a good point about the unlikelihood of killing him outright. I was basing that on the idea of the previous encounter where I would cast Evard's and then head off to the other encounter. By the time I got back he might've been crushed. So, yes, if I got him when I could watch him I could dispel it before he's dead (unfortunately, though, my 'rookie' character might think he was bluffing, or might actually fall for a bluff).

 

[radmod]

Stinking Cloud is good. Lob in Kelgore's Grave Mist and Death's Call for exhaustion winsauce if you'd like the irony of using necromany spells against him. I'm assuming that you've got some way of spontaneously quickening spells

I should've mentioned that, my specialty is Abjuration and I don't do Necro/Illusion (only 'bad' guys do those, right?). As a UM, yes, I can Quicken easily.

Stream : "You're not up on noncore spells, but you're using a PH2 class, the beguiler."
Yeah, I know, kind of stupid. I had to create the character quickly and I wanted to double down on my high INT. I've yet to get a chance to really read up on things.