Diath is a composed and calculating individual, comfortable serving as a leader to his friends. He is often quiet, at times speaking only when it is pragmatic, and he is always alert to signs of danger. He cares deeply for his friends and has made immeasurable sacrifices for them over the course of their adventures.
Background (spoilers for Season 1) Edit
Diath's true backstory is unclear, as there are major differences between his character sheet and what is later revealed by Chris Perkins in Season 2. According to his character sheet, he was born in Waterdeep to a hard-working middle class family. When he was young, however, his family home was burglarized, and he had to resort to working odd jobs or begging in the streets to help his family get by. Being a victim of crime is the reason he refuses to turn to thievery himself. One day while begging in the streets, a cloaked man placed a mysterious ring of keys into his hands, which Diath has kept on him ever since.
He eventually turned to adventuring as his main source of income, but believed that the stories and experiences he gained were more valuable than any amount of gold or gemstones. However, he does keep an amethyst as a pendant around his neck, which was his first successful plunder of an enemy lair. Several years before the start of DCA, he ran into Strix, who was foraging for food in the alleys of Waterdeep. He eventually earned her trust, and they decided to team up. They met the rest of the Waffle Crew at the Rusty Pommel Inn, where the group decided to flee after Diath was falsely accused of pick-pocketing the barkeep. The party had several adventures together before being mysteriously summoned to the land of Barovia.
Once there, Diath had a vision where he saw himself hanged. This in fact came to pass in the town of Vallaki, where he came to the attention of Izek Strazni, Strix's half-brother. Diath had killed one of Izek's fellow henchmen and was placed in the stocks, but rather than eventually freeing him, Izek took his life. This event was marked by several odd occurrences, such as ravens attacking anyone nearby, time seeming to slow, and a skull appearing in the clouds. Diath was trapped as a wandering spirit, but was able to temporarily possess Paultin. He was eventually revived by the abbot of St. Markovia's temple in Krezk. As a side effect, he suffered a temporary resurrection madness that made him as fearful as Strix.
The Waffle Crew eventually traveled to the Amber Temple, where Diath almost died again. Hoping it might heal him, Strix poured a potion of youth into his mouth; however this only succeeded in turning him into an 18-year-old. Strix was then killed by vampires. To revive her, Diath made a deal with the Dark Power named Zhudun the Corpse Star to receive the one-time dark gift of greater resurrection. Ironically, before he could use it on Strix, van Richten appeared and gave them a scroll to raise the dead. Together, they raided the temple and found the Tome of Strahd that had been foretold in Diath's Tarokka card. He used one of his mysterious keys to open the lock on the book, and they learned about Strahd's dark past. van Richten revealed that to trap Strahd's soul, they needed the blood of a powerful Vistani. Diath made the difficult decision to kill a young Vistani seer, an act that was observed by the sentient puppet, Simon. Simon had also instinctively reacted and killed a Vistani child, although ironically, Diath did not sympathize and could only think of the construct as evil.
Unfortunately, as a cost to receiving the dark gift, Diath began slowly turning into a ghoul. This was reversed when they entered the crypts of Ravenloft and Diath imbibed a potion made with St. Markovia's holy ashes.
Character development (spoilers for seasons 2 & 3) Edit
Upon leaving Barovia for the frozen north, Diath and the Crew were set upon by werewolves trying to recover the effigy holding Strahd's soul. To protect them, Emil offered to turn the Crew into werewolves, which Diath agreed to very reluctantly, even though it was only temporary, since he cherished his humanity now more than ever before. They also ran into Simon, who Diath developed an intense distrust and dislike for, even though Paultin and Evelyn had chosen to befriend him.
During a mission to spy on the fire giants for the dwarf king of Citadel Adbar, the Waffle Crew accidentally triggered a chain of events that led to the destruction of the giants' reforged colossus. Diath also unintentionally killed the prisoners he had been trying to save when he found himself unable to command a fire primordial that he had released, which proceeded to go on a deadly rampage and destroy the mountain. Those deaths weighed heavily on Diath's mind, and he began to doubt himself as a leader. He even re-evaluated his hatred of Simon, choosing to pay for it to be rebuilt.
Shortly after Evelyn had sacrificed herself in a ritual to make rings to protect Diath and Strix from the death curse, a half dwarf-orc thief tracked down Diath and handed him the sentient magical sword Gutter, which had belonged to the dworc's adventuring companion, Ashton Woodrow. At this point, Diath's backstory diverges slightly from the character sheet, with Chris calling Diath an 'orphan' who came from 'the gutter', and Jared confirming that Diath knew nothing about his parents or who Ashton was, and that he was sold as a child (however, in a later episode when inside a Zone of Truth, Diath admitted that Ashton was actually his dad, but that he was "no father of mine"). Gutter had possessed the dworc's mind to have it carry the sword to another member of the Woodrow family. Gutter then spoke to Diath's mind, suggesting that he place one of his keys in the sword's keyhole near the hilt. This summoned the arcanoloth Shemeshka, who revealed to Diath that she had made Gutter for Diath's ancestor, Dareth Woodrow, and that using the keys would grant him three answers from her. Diath was soon after summoned back to Barovia, along with the rest of the Crew, when the Dark Powers attempted to use Paultin in a ceremony to revive Strahd. The Crew foiled this attempt, but were then transported to an earlier timeline in Barovia, before Strahd's conversion. Rather than confront Strahd with the truth directly, the Crew attempted to poison him, help Tatyana and Sergei flee the castle, and convince his chamberlain that Strad was evil by showing him the Tome of Strahd. The plan failed, and Diath, Paultin, and Evelyn were killed and their spirits wandered the mists for 50 years until Strix's friends revived them. Strix had been very mentally and emotionally troubled during those years alone, crafting dolls in the Crews' likeness, although it had been especially difficult to make Diath's.[13,14] Holly later admitted that although Strix initially did not understand relationships or intimacy, her time in isolation made her open to experiencing deeper connections with others.
Diath has shown hints of having strong feelings for Strix throughout the series. Perhaps subconsciously, he began to make connections between her and his amethyst: things that others may disregard at first glance, but that he's held on to because he sees their true value. When they infiltrated Barovia in the alternate timeline, Diath even called Strix 'Amy' (short for amethyst), telling her it was her secret name. When Strix vanished from the deck of the airship, Diath immediately summoned Shemeshka to find out where she went. Shemeshka told him that she was summoned by Omin Dran, and droped hints that Diath was a Lorcatha (a word Izek called him in Barovia) and that the 'Skizziks' were after him. In Chult, the Crew were confronted by a Mercykiller who tried to bring Strix back to Sigil, saying the Skizziks kazram hired him to bring her to them. When Diath intervened, the mercenary took him instead, again hinting that the Skizziks didn't like 'his kind', the Lorcatha. Although they were only briefly in Sigil before managing to escape, Diath did note the presence of the mysterious stranger that had given him the keys. Kerrek the paladin was the only one to notice that the stranger's face was actually half-angelic. When they were finally able to catch a peaceful rest, Diath admited to Evelyn his feelings for Strix, and she encouraged him not to lose hope. Diath also expressed to Evelyn his admiration for her, and that he trusted her to guide him to do what's right.
In Dendar's temple, Strix and Diath both were subjected to a mass hallucination where they imagined themselves transported to different realms. Strix saw herself trapped in a maze with Ubtao, who revealed to her that the Lorcatha have ties to celestials, and were long ago at war with the Skizziks. The war ended in an accord where all but one Lorcatha lost their soul, and the two families had to agree to have nothing to do with one another. In Diath's hallucination, he saw himself losing a pair of angel wings, and being confronted by an evil Paultin taken over by the Ring of Winter. He also saw what he thought was Strix, but was actually a swarm of cranium rats inhabiting her clothes. They mocked him saying, 'we are many, you are one'.
After the Crew followed Paultin into the Shadowfell, Diath fell into a magical despair and became unable to tell what was real (he also thought he saw a shadow of himself hanging from a tree). They then ran into Izek, and although Strix told Diath to stand down, Diath kept Gutter or his poisoned dagger at the ready around him, refusing to trust him. Izek confirmed that their two families had been at war for "eons", but that after the Skizziks allied themselves with Asmodeus and became tieflings, the Lorcatha allied themselves with celestials, and the war escalated to cause the deaths of millions. Izek said Asmodeus and other Powers had a hand in forging the Ashtown Concordance, where Asmodeus got to keep all but one Lorcatha soul, but the deal forbids the two families from sharing any other alliance or friendship. Despite this, Strix and Diath refuse to be intimidated, and Strix now holds one of Diath's keys, and Diath possesses Strix's doll she made of herself.
Notable Equipment (spoilers for season 3) Edit
- Mysterious Ring of 9 Keys - Diath received them from a stranger as a child. He has already used 6 keys (1 on the locked Tome of Strahd, 4 keys in Gutter (ep 53, ep 61 x2, ep 80) and 1 on the force bomb) and given one to Strix for safekeeping.
- Gutter - a sentient magical short sword of backstabbing forged by Shemeshka for Dareth Woodrow and her descendants. It has a keyhole where the hilt meets the blade, which can be used to summon Shemeshka when one of the magical keys is placed inside to make her answer three questions. The name Gutter is inscribed in the blade in Abyssal runes.
- 2 gourds of "sticky poison" for coating weapons (+1d6 to attack) (one gourd was used to apply poison to one of Diath's throwing daggers in ep 83)
- ring of protection +1 (blessed by St. Markovia)
- magical stone of good luck - given to Diath by a young halfling girl as a sign of appreciation for saving her. Also known as the "butt rock" or "butt stone".
- amethyst pendant - the gem was loot from one of Diath's first successful treasure hunts. He later began to compare it to Strix, describing it as something others have told him to get rid of, but that he holds on to because he can see its true value. Shemeshka examined it and said it was non-magical.
- Gloves of Thievery
- Horn of Blasting (given as a reward by the grung)
- shards of Lightfall (broken double-bladed battle axe emblazoned with Lathander's holy symbol, further empowered as a mace of disruption) (bequeathed by Evelyn)
- extremely sharp crystal shard of Ligotti, K'thiss's sentient crystallized tentacle 
- masterfully crafted mysterious locked padlock found on the corpse of Krezk's burgomaster's son, that gives off a sense of unease 
- Tome of Strahd - Strahd's journal, describing his pact with the Dark Powers and his tragic love for Tatyana. Diath gave it to Rahadin to try to convince him to join their side, but the dusk elf burned it
- doll of Diath (roughly constructed doll made in Diath's likeness by Strix during her 50 years alone in Barovia)[13,14]
- doll of Strix (roughly constructed doll made in her likeness by Strix herself, after she destroyed the original she had made)[11,14]
- Jared has used Diath Woodrow as a character in numerous D&D campaigns prior to the start of DCA
- Jared wrote a piece concerning Diath's thoughts during the events of Episode 58. He also wrote a short fic regarding Diath's thoughts while watching Strix make pies.
 DCA Episode 73.
 DCA Episode 8.
 "I'm Jared. I play Diath Woodrow. AMA!" DCA Reddit.
 DCA Episode 18.
 DCA Episode 23.
 "Ask the Wafflecrew Anything Panel at PAX West". Twitch.com.
 DCA Episode 30.
 DCA Episode 33.
 DCA Episode 53.
 DCA Episode 85.
 DCA Episode 58.
 "Is Diath's amethyst analogues for Strix?" DCA Reddit.
 DCA Episode 60.
 DCA Episode 69.
 DCA Episode 79.
 WafflesInc Secret Santa Gift Exchange. DCA Reddit.
 DCA Episode 13.