D&D 5E The Smooth Talker

Yes - my character in a Tuesday night game.

Lore Bard, with Expertise in Insight and Deception, and proficiency in Perception, Persuasion, Stealth and Sleight of Hand. Highest ability scores are CHA then WIS then DEX. The character is a spy for the government. As a tiefling, she's pretty memorable, so she steals secrets not by being unnoticed, but by making sure no-one associates the well-connected Tiefling (who had a valid reason to be there) with any security breach.

"That Tiefling? Nah, mate, she's no spy, she's the quartermaster's assistant for the army base at Emmech. Tom's mate Erin knows her from when she was posted there. "

Between a short sword, a crossbow, and vicious mockery, she's plenty effective in a fight, especially when every combat starts (and once, ended really quickly) with a sleep spell.

In the exploration tier, she has detect magic and comprehend languages as rituals (both just as useful in a dungeon as in an enemy town hall) as well as Perception and Thief's Tools proficiencies. Over half the party has stealth, so on one occasion the "scout ahead" group was ¾ of the party!
 

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This and this again. While Charisma can be said to represent knowing how to say what you need to say, Wisdom can also be said to represent knowing WHEN to say what you need to say.
On the other hand, there's a long-running precedent for smooth talkers not knowing when they should shut up. Huck Finn, Groucho Marx, Bugs Bunny, Han Solo, Tony Stark, 90% of George Clooney characters...
 

My money's definitely on Bard, though Warlock plus a level of Rogue isn't a bad choice either.

With Lore Bard, you'll have 8 skills innately (3 Bard, 3 Lore, 2 Background), and picking Half-Elf gives you another two skills; that plus Jack of All Trades means you're never going to suck at any skill-related thing, and Expertise makes it even better. Plus, Bards get several spells that are useful for Charisma stuff, and Lore gives you extra Magical Secrets, just in case you're missing any spells you really wanted.

Put your first two Expertise choices into Insight and your preferred social skill (presumably Persuasion or Deception). Put the next two Expertise choices (if you get any) into the other two Cha skills (Intimidate and whatever you didn't choose of P/D). If you max out your Charisma by level 8, then by level 10 as a Bard you'll have +13 total to all social skills, and you can easily swing a 14 Wis to start with, giving Insight a +9. You'll be better than the best non-Expertise person at every social skill without magic, and if you bring in things like calm emotions, enhance ability, disguise self, command, or suggestion, well, it'll be goddamn hard to stop you. And that's just first and second level spells!
 
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New Feat: "Manipulator"

- Increase Charisma by 1
- Add your Wisdom or Intelligence modifier to your Deception, Intimidation, and Persuasion rolls (in addition to Charisma modifier.)
 

Don't overlook the Enchanter Wizard. An at-will charm can be pretty insane, but you need to maximize Int and Chr in this scenario if you want to capitalize upon it.
 

Don't overlook the Enchanter Wizard. An at-will charm can be pretty insane, but you need to maximize Int and Chr in this scenario if you want to capitalize upon it.
Problem is until 14th level most charms suck for out of combat actions as the target remembers and is pissed about it. If you plan on being long gone once the charm breaks it's okay. But it's a narrow campaign that this works for. I don't disagree with the general rule on charms but I wish that ability came in much sooner.
 

If your GM allows it, the Order of the Awakened Mystic from Unearthed Arcana would be pretty good. They can get expertise for one skill, can take a greater discipline at 5th level to get 1/2 Int mod to Charisma checks, and have a handful of charm and mindreading sort of abilities.
 

See targets on page 204 of the PHB. Creatures that are the targets if spells with no obvious effects do't necessarily know they are under a spell. Dominate a monster and force them to do somethig? Obvious magic. Charm a monster and persuaded to do something you wanted to do and it may never know that you've influenced it... unless the Spell says they know (like charm person). Hypnotic Gaze has no such limitation. If you hold them locked in a trance for hours, that is obvious magic. Hypnotize them for a few seconds while you suggest a reasonable activity... perhaps they never realize you influenced them magicalyy. It is all up to the DM.
 

I'm thinking about trying out a Smooth Talking character build during my next campaign. I want him to be able to persuade or decive his way out of just about any situation. The DM has allowed just about any unearthed arcana. My questions are, have any of you ever created a character like this? What class works best (bard was my thought, though I could also see rogue or sorcerer)? What feats would be worth picking up? Any other ideas or tips would also be appreciated :)

I'd totally play a mastermind rogue: http://media.wizards.com/2015/downloads/dnd/SCAG_RoguishArchetype_m39d.pdf

Feats I'd look at are Actor, Inspiring Leader, Linguist, and Observant.

Most background features have a social component (save Hermit or Outlander) so any background could work for a "Face" character.
 

If UA is OK, can you use Changelings? If so, that is hands down the best social guy I think and shockingly OP IMO. A Changeling Mastermind is the way to go I think. You can be as great at communication as you want, if you look like a target, the orcs are going to kill you before you open your mouth.

There is little point using changeling abilities to infiltrate and area, then not having the combat, stealth or lockpicking to open the place up for your allies. A Swashbuckler rogue would be a good option too, as you will often find yourself alone as a Changeling and their movement and combat abilities lend themsleves well to that. Sure an assassin makes great use for being a Changeling, but that is a different character concept.
 

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