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I am rolling a Human Charlatan rogue for a Pathfinder campaign, Starting at level 3. I am looking for any lesser known tips/skills/feats to increase my charisma/bluff skills.

I am working off 3.5, but the DM is extremely relaxed, basically if I can find documentation for it, he'll allow it.

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    \$\begingroup\$ @ShadowKras has made a noble attempt at answering this question as it stands, but refining this question would allow that and other answers to focus more on the question's precise situation. Clarifying exactly what's meant by "tips/skills/feats to increase… charisma/bluff skills" is step 1. There's no way the site can list in one answer every possible way in 3.5 and Pathfinder to do that, even if the PC's only level 3. \$\endgroup\$ – Hey I Can Chan Dec 30 '16 at 18:23
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Feats

There are the obvious Skill Focus (Bluff) (+3 to Bluff), and Deceitful (+2 to Bluff). The ultimate intrigue also brings Blustering Bluff, which allows you to basically re-try to tell a lie telling another lie and decreasing the DC of the check.

Traits

There is a fair amount of traits that grant +1 to bluff, you can check those here (just filter by "Bluff").

Mundane Items

There are two cheap and useful items to obtain a quick bonus on Bluff checks:

Blue Book: By consulting the book for 1 hour, for the next 24 hours you gain a +2 circumstance bonus on Knowledge (local), Bluff, and Diplomacy checks to gather or use information in that city.

Perfume Kit: Applying scents from a perfume kit takes 1 minute, and grants you a +1 circumstance bonus on Bluff, Diplomacy, Disguise, Handle Animal, Intimidate, or Perform checks, subject to GM discretion.

Magic Items

The Mask of Stony Demeanor may be too costly at your level (8,000 gp), there are a few others that could be helpful: Ring of Eloquence, Veil of Veils, Cracked Mulberry Pentacle Ioun Stone, and the Honeytongue Elixir.

Class

Honestly, there are better classes to pick when the point is to make a good bluffer, such as bard, investigator, or even a Spy Rogue. But since your choice is already set, there isn't much we can do here. Except for Rogue Talents.

Rogue Talents

Rogues have quite a few abilities to improve their Bluff skill usage.

  • False Friend gives +4 to Bluff checks against those you never met before.
  • Honeyed Words allows you to re-roll a Bluff check once per day.
  • Coax Information allows you to use Bluff to intimidate someone to act friendly towards you.
  • Convincing Lie is a tricky one. Basically it makes people use your own bluff modifier when passing along your lies, basically spreading them like wildfire. So, if you are a truly exceptional liar, no one will ever question it.
  • False Attacker allows you to trick someone who you just backstabbed from the shadows into believing that someone else did it (no, seriously, take a look at it).
  • Innocent Facade allows you to use the Innocense spell once per day, which grants a +10 on Bluff checks to convince others that you are innocent.
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  • \$\begingroup\$ Admiral's Bicorne (Stormwrack), for 51,000 gp, +5 to Cha-based skills (among others) has been analyzed to theorize that +N to all X-based skills would cost N*N*500 gp. In the same vein, +N to a single skill costs N*N*100 gp. For a temporary bonus though, Glibness is +30 to convince others you tell the truth, and you can get wands/potions of it... \$\endgroup\$ – Matthieu M. Dec 30 '16 at 20:07
  • \$\begingroup\$ Good point, you cannot make potions of Personal range spells though. Wands are fine, but the price would probably be outside his budget (being lv3). A Wand of Glibness would cost him 13,500 gp. \$\endgroup\$ – ShadowKras Dec 30 '16 at 20:27
  • \$\begingroup\$ The bracers of Glib Entertainer would be an option, allowing to cast Glibness once per day, but costs 7,900 gp. \$\endgroup\$ – ShadowKras Dec 30 '16 at 20:29
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    \$\begingroup\$ A partially charged wand, or a few scrolls, could be an option for restricted budgets. \$\endgroup\$ – Matthieu M. Dec 31 '16 at 12:43
  • \$\begingroup\$ Don't forget the Circlet of Persuasion d20pfsrd.com/magic-items/wondrous-items/c-d/… \$\endgroup\$ – TVann Jan 21 at 15:10

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