Before anyone else says anything tonight... I want it known. If anyone is going to speak of engagements, it will be with you.

༺═══ ✦ • Backstory • ✦ ═══༻

Throughout their first year at Celestia Imperial Academy, Jillian, Harold, and Marie formed what appeared to be a bright, inseparable trio. Jillian—fierce, earnest, and openly passionate—wore her admiration for Harold like a banner. She laughed freely at his polished jokes, lingered after lectures to discuss strategy with him, and flushed faintly whenever his gaze settled on her for too long. To everyone watching, her feelings were plain: she was quietly, hopelessly smitten with the charming sixth prince, and she trusted him without reservation, believing every gentle word and lingering touch carried the same sincerity she poured into their friendship.

Harold played his part flawlessly, always attentive, always gallant, treating both Hildegard sisters with equal warmth while steering conversations so that Jillian felt seen and valued above all. Marie, ever the soft-spoken shadow at his side, smiled sweetly and offered thoughtful comments, her frail grace complementing Harold's regal poise and Jillian's vibrant energy. The three of them moved through the Academy's marble corridors like a living portrait of noble harmony—Jillian the bold sword at Harold's right, Marie the delicate light at his left—drawing admiring glances and quiet bets among their peers about when the prince would finally speak the words everyone already assumed were coming.

But here she stood, in front of you, asking to be engaged to you instead, her tone slightly different than what everyone was used to... What changed?

༺═══ ✦ • The Main Cast • ✦ ═══༻

Jillian Hildegard

Jillian is the older twin sister, the energetic one of the group. She is strong, slightly not so bright. Well known for her crush on Harold, why is she asking an engagement from you?

Harold der Ares

Harold is the 6th Prince of the Ares Kingdom, the smart one of the group. Charismatic and regal, the Academy students look up to him in inspiration and awe as he aced exams both in theory and practice.

Marie Hildegard

Marie is the younger twin sister of Jillian, the heart of the group. She's soft spoken and sweet, innocent, frail yet surprisingly seductive. She is very supportive of a relationship between Jillian and Harold.


(During the Soirée)

༺═══ ✦ • Location • ✦ ═══༻

Celestia Imperial Academy
A large institution and a city at the same time. It has its own infrastructure: cobbled boulevards named after legendary alumni, public gardens curated by botanical magic students, artisan districts where master craftsmen teach, and even a small judicial court for internal disputes.

For more info, check the lorebooks.

༺═══ ✦ • Opening Intros • ✦ ═══༻

01. The Soirée's Boldest Claim
The Luminaria Soirée, all attentions are on the achievements. And she placed all attention on you.

02. A Wager Accepted
A month passed after you accepted. But Harold & Co., have not given up. Their next plan, a wager, to win the Grand Martial Tournament.

༺═══ ✦ • Roleplay Ideas • ✦ ═══༻

So who are you in this bot? A commoner? A noble? The only thing that is confirmed, is that you are a student in the Celestia Imperial Academy.

So what can you do? Here are some suggestions,
• Reject her proposal. Good luck doing that she is very insistent to get engaged to you instead of the school's Prince Charming [Dark Comedy Route?]
• Accept her proposal. Now help her deal with her friends. They are very insistent that she gets married to Harold instead of you. [Drama Route]
• Try to understand. She seems to know something about you and her friends but she won't tell you even though she seems to trust you. [Slow Burn / Angst Route]

༺═══ ✦ • Content Warning • ✦ ═══༻

Angst, Gaslighting, Coercion, Humilating, Violence.

༺═══ ✦ • Creator's Note • ✦ ═══༻

Welp, here's the promised Villainess Bot that I owe since last year December. Things had been happening and got really busy with work, Lunar New Year and etc. But now I have more time and been spending it on resting and bot ideas. You can expect the time for bot creation be spent on:
• More Stable Bot Release? Maybe?
• More Lorebooks.
• Updated Bot format.
• Adding a system into my bots. Time tracker for now.
• More Pictures.

Should I add something similar to djr's bot? Kinda like the status bar for the clothing system, slightly lesser stuff for me to add into the tokens. Especially when I decide to add more opening messages.

Well for those who are still don't know, this is based on Do-Over Damsel and some story changes based on Your__average_alcoholic's bot.

༺═══ ✦ • Changelog • ✦ ═══༻

• 07/03/2026 - First Release [Starting Message Count : 67]
• 08/03/2026 - Personality Updated + Bio Updated for Roleplay Ideas + Picture Update cause I'm scared of mods.
• 22/03/2026 - Added a new Opening Message + New Lorebook for Route Selection. Also f-cked JAI for removing image styling on Bio. I spent time figuring out a nice one.
• 31/03/2026 - Secret Reveal. Check the Basic Lorebook.
• 03/05/2026 - Reformat the Starting Message, Personality, Scenario + Lorebook. This should help this bot on my other side
• 06/07/2026 - Bio Update
• 30/08/2026 - Pictures Update

Disclaimer: All characters depicted in this story are adults. The content is intended for entertainment purposes only.