Socialite

The smooth talking trader brings his new customers into his store, after all, who could resist his new Snake Oil? Socialites push their wit and charm to the very extremes, swaying politics or creating mobs to do their dirty work.

Bonus Proficiencies

When you become a Socialite at 3rd level, you gain Proficiency in the Persuasion Skill if you don’t already have it.

Saving Face

The pressure to succeed is an ever-present one, with failure meaning a loss in reputation.

At 3rd level you gain a bonus to to any rolls you have Disadvantage on equal to your Charisma Modifier. 

In addition, after failing a skill check you may choose to reroll your save 2 times per Long Rest. This increases to 3 times at 9th level, and 4 times at 17th level.

Winning Smile

Your charm is almost irresistible. When you reach 9th level in this class, you may, as an action outside of combat, initiate a Charisma (Deception) contest against a group or individual that can hear you. If you succeed, the target is Charmed for 24 hours, or until attacked by you. The target won't risk their life for you, but they will take your side in a debate, or defend your honor. If you fail, the target is unaware of your attempt to charm them and cannot be Charmed in this way again for 7 Days. In addition, you have Advantage on attacks on anyone charmed by your Winning Smile. You may use this ability once per Long Rest.

Success by Association

When you reach 13th level in this class, you and your allies can share your modifiers to make saves. When you and your allies are must make a save at the same time, you can choose to use the greater of your modifiers. For example, if you and an ally must make a saving throw against a Fireball, your ally may use your Dexterity Modifier to make the save if it is higher than their own. In addition, if you and your allies are making a Dexterity Save, they gain the benefits of your “Elusive" ability. This ability does not apply to creatures who must fail the fail the save through conditions or effects.

I Rest My Case

When you reach 17th level in this class, your skills of debate can be used to assault the ego of your targets. Twice per Long Rest, you may roll a Charisma (Persuasion) Contest against a targets Wisdom (Insight) . On a success the target takes your sneak attack damage as Psychic Damage. On a failure, the target takes no damage and is aware of the attack on its mind. In addition, targets Charmed by your Winning Smile automatically lose the contest. The target must share a language and be able to hear you in order to affect them.