Arc 1Chapters 1–25
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After transmigrating as Greg Sass, a doomed villain in a dating game, Greg used his dungeon talents and game knowledge to survive underground. On day five, he saw the protagonist Victoria reaching for Sylvia as Sylvia sank in the river, a scene he had never encountered in the game.
Greg saved Sylvia from a Blackwater Octopus in the underground river, then encountered Victoria and tried to explain his past actions. A new redemption quest appeared, requiring him to clear the Dungeon’s first floor before the end of the first act or face another death.
Greg persuaded Victoria that he was a goddess’s emissary seeking to conquer Dungeons, though she remained wary of him. After Victoria brought the unconscious Sylvia to Greg’s cave, she unpacked two mysterious items, prompting Greg to shout at someone about a gray-haired brat bringing a care package into the Dungeon.
Greg persuaded Victoria to throw away two dangerous objects that could trigger scripted deaths, then denied kissing Sylvia after she woke. Sylvia revealed that the Holy Light Church could test whether Greg truly served the Goddess of Night, leaving him worried about being exposed.
Greg's invented claim that he was an emissary of the Goddess of Night was confirmed by Sylvia's test, which also revealed that a holy seal covered his vital parts. After learning that the current saintess might be able to remove it, Greg realized he would need to find a way to get her help before Sylvia became saintess.
Greg gave Victoria a rare reflection Gem in exchange for her and Sylvia's help clearing the Dungeon's first floor after their class placement assessment. After Sylvia delivered Ellie's threat to enter the Dungeon and kill herself if Greg did not appear within a week, Greg realized she might mean it and wondered how much time remained.
After leaving the Dungeon, Victoria and Sylvia reconsidered Greg’s motives, while Victoria held on to the Gem he had entrusted to her. Three maids mistook Victoria for the red-haired second princess, Lilith Kahn, and revealed that Lilith had run off again as Victoria hurried away to practice magic.
Greg discovered that he had gained Dark Magic Affinity LV10 and two dark magic skills, raising questions about the Goddess of Night. Meanwhile, Lilith Kahn entered the Dungeon alone and was dragged underwater, where an unknown rescuer caught her wrist.
Lilith Kahn was rescued from drowning by Greg Sass, whose calm behavior contradicted the rumors she had heard about him. After following him to repay her debt, she watched him effortlessly defeat monsters and prepare to cook, leaving her astonished by how different he seemed.
Lilith visited Greg’s Dungeon camp and learned that Victoria and Sylvia had recently made peace with him. When she asked how they compared with Her Highness Lilith, Greg answered with a crude remark about their bodies, leaving Lilith furious.
Greg told Lilith that Victoria would defeat her in the upcoming Class Placement Duel, explaining that Victoria’s combat experience could overcome Lilith’s powerful magic. Lilith remained unconvinced, but Greg’s grilled meat skewers impressed her, and she silently admitted they were delicious.
Lilith returned to the dormitory after spending the evening with Greg Sass, then privately reflected on her growing ease around him and her fear that he would treat her differently if he learned she was a princess. As she prepared for the next day’s class placement assessment, Greg called out to the Goddess of Night, who appeared as a black cat.
Greg confronted the black cat and learned that she was the Goddess of Night, whose mark had bound their fates together. She revealed that his death would also kill her, and that he could now be considered a deity.
Greg learned that he had become a demigod through his bond with Nightmare, the weakened Goddess of Night, and that their lives were linked. After Nightmare named him the Dark Night King, Greg asked why she had chosen him.
Nightmare told Greg that the Five Great Dungeons were prisons sealing dangerous Outer Gods whose awakening could destroy the world, and claimed Greg had the potential to conquer them. Greg rejected her account and refused to explore the dungeons willingly, trusting that the Demon King—not these unknown beings—was the world’s real threat.
Greg postponed leaving the Dungeon to find Ellie until the following night and worried about the class placement assessment. Lilith woke from a dream about Greg, tried to convince herself their meeting had been imaginary, and learned from Laila that she had made a new friend.
Lilith prepared for the Academy placement exam determined to prove Greg Sass’s prediction wrong, while Victoria resolved to defeat Lilith in their first official match. Both headed to the Martial Arena confident they would win.
At the Academy’s class placement assessment, Victoria stood up to noble students who insulted her and Greg Sass, drawing Princess Lilith Kahn’s support. Lilith challenged Victoria to their upcoming match, and the two met as eager rivals.
Grace Quinn began the placement assessment, and Sylvia Lorraine earned a place in Class A by defending against Angela White’s wind magic with a powerful Wall of Light. Victoria Cecil and Princess Lilith Kahn were announced as the next pair, leaving their match about to begin.
Victoria Cecil and Lilith Kahn began their highly anticipated duel, testing each other with fast, powerful spells. Victoria weathered Lilith’s opening attacks, and Lilith grew cautious as she recognized the commoner’s skill.
Victoria fought Lilith Kahn in the Class Placement Duel, hoping to trick her into using Flame Explosion and then evade it. Lilith anticipated Victoria’s feint and aimed the spell into the pit where Victoria had taken cover, leaving Victoria’s fate unclear after the explosion.
Greg woke in the evening and set out to sneak out of the Dungeon to stop his maid from becoming a terrorist. At the Academy entrance, he collided with Lily Carlo, who appeared to be sneaking into the Dungeon herself.
Lilith snuck out to tell Greg that she had beaten Victoria, but their awkward encounter left her blurting out the news as she ran away. Greg realized only after she had gone that Lilith had won with Flame Explosion, contrary to what he had expected.
After losing to Princess Lilith, Victoria hid her distress from Sylvia during a hospital visit, then confronted her own pain and doubts about whether she could fulfill her vow as the Hero. She remained alone in her hospital room, questioning whether she was strong enough to protect those she cherished and take revenge on the Demons.
Victoria reflected on her failed plan and her complicated feelings about Greg, while Greg rushed into the wrong hospital room and mistook a bandaged patient for her. The chapter ended when Victoria appeared at the doorway and Greg realized the patient in the bed was a stranger.