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Weapon (dagger), very rare
A set of knives; although they come in a massive variety, all are unassuming, noticeably old and raggedy. Some, however, have specks of dried blood left on the blade, or the handle. You have a +1 bonus to attack and damage rolls with this magic weapon.
Serial Killings.
Whenever you reduce a creature to 0 hit points with a melee attack made using Jack-of-Smiles, you can use your bonus action to move up to 10 feet and make another melee attack.
Slasher.
Attacks made using Jack-of-Smiles score critical hits on attack rolls of 18 and above; when they do, roll all of the attack's damage dice a third time and deal that much additional slashing damage.
Undying Infamy.
While wielding Jack-of-Smiles, you gain a +1 bonus to and have advantage on Charisma (Intimidation) checks. Whenever you make a successful melee attack against a creature, you can use your bonus action to make a Charisma (Intimidation) check with DC equal to 12 + their Charisma modifier; on a success, the target becomes frightened of you for 1 round.
Sentience. Jack-of-Smiles is chaotic evil, and has an Intelligence of 7 (-2), a Wisdom of 12 (+1), and a Charisma of 18 (+4). It can hear and see to 60 ft., and has darkvision for 30 feet. It can understand Common and sense the general emotions of those around it; it can only speak telepathically to its current holder in short words or phrases, but can inspire emotions in them.
Personality. Although the name is commonly used to talk about those wielding the knives, Jack-of-Smiles is technically a personality housed in the weapons themselves. Jack seeks to cause as much mayhem and bloodshed as possible, with the goal of becoming infamous and renowned; each knife in the set has the same simple personality, encouraging anyone who touches one to go on a brutal killing spree and attempting to take over their body if they resist. Since this almost invariably leads to their owner's violent death, and since they can easily be lost, broken, or locked away in the aftermath, individual knives have little chance to mature beyond most straightforward methods. Nonetheless, the sheer number of them ensures that at least one or two "Jacks" exists at any given time, no matter how often he (or she) is killed.
Jack was created with the goal to produce love stories through tragedy, although his blunt methods and the repetitive nature of his killings have largely made this a failure.
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