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Diplomancer's Ring
Rarity: Very Rare
Aura: Enchantment (Strong)
This ring appears to be an ornate precious metal ring with numerous large inset gems; often, it is sized for the largest finger of a medium humanoid creature, which may fit it to the smallest finger of a large humanoid creature, or on the thick thumbs of a small humanoid creature. The ring is extravagant enough to be noticeable from afar, if unobscured; creatures prone to greed or thievery may find themselves envious.
The wearer is granted a silver tongue, the visage of a pleasant appearance to all aesthetically-inclined creatures, and an unmatched eloquency.
When worn, as long as the ring is unobscured: the ring grants both proficiency and advantage on all CHA-based skill rolls, and proficiency with CHA saving throws which stacks with other bonuses. Additionally, for any CHA skill, check, or save, before counting a roll toward advantage: reroll any 1s, as with the Lucky feat. Any creature with which the wearer interacts must make a WIS save, DC 15; on failure, that creature is charmed by the wearer (though this doesn't add yet more advantage--it merely affects that creature's demeanor and ability to retaliate). The charmed status is revoked when the wearer leaves the creature's vision, or if all Diplomancer's Rings are removed or become obscured.
Any spellcaster knowing Charm Person can create this from a ring of sufficient quality by casting d100 consecutive slightly-modified Charm Person spells on the ring at touch range (multiple casters may need to be present if this exhausts one caster). The DM may raise or lower the result of the d100 roll based on the quality of the ring.
AC and HP are inherited from the progenitor ring. When it is destroyed, no particular effect occurs beyond what would happen if it were removed.
Per Detect Magic, this ring has a strong aura of enchantment.
When wearing multiple such rings, the effects do not stack, but charmed statuses terminate only when the last ring is removed or obscured.
This is an overt homage to the famous "diplomancer" played by Chris Harding in some of the infamous Jake Woods campaigns--although I've only heard tell and never seen the legend, rumor has it that the diplomancer was a high level wizard with ridiculous Diplomacy, Bluff/Deception, etc., and a spell roster focusing on enchantment. Hilarity ensued whenever battle broke out, and the high-level wizard would be trying to argue for "diplomatic" solutions to invading fiends or hordes.