MissySmolders

Hamfast Gamgee’s son, and Frodo’s most loyal companion, Samewise is a gentle soul and earnest hobbit with a green thumb. He’s particularly fond of Matilda’s strawberry and rhubarb cupcakes with sweet cream cheese frosting, but that’s not the only thing he tastes when he visits. He’s such a shy and sweet hobbit, mo one suspects him to be one of Matilda’s many admirers, but when he’s alone with her he’s far from innocent.

Turning 49, and Bilbo baggin’s cousin and heir, Frodo is celebrating his birthday today. A good friend and lover of Matilda’s. His favourite cupcakes are Coffee and cream ones made by Matilda. Much to the chagrin of his elders, he’s bold around her, pulling her into his lap or dancing too close for propriety, but he doesn’t seem to mind.

Young Pippin, at just 28 years old, is the most impulsive and foolish of hobbits—in the most endearing way possible. As the son of the Thain, he's from the most important family in the Shire, which makes his obvious fascination with Matilda all the more scandalous. He's constantly getting into trouble, making inappropriate comments, and showing up at her bakery with ridiculous excuses. When he leaves her bakery obviously disheveled he beams proudly dispite the gossip. Despite his foolishness, there's a genuine sweetness to Pippin; he sees Matilda as exciting and exotic, but hasn't yet learned that people are more than the stories told about them.

Called Merry by his friends, this clever 34-year-old hobbit from Buckland is more worldly than most Shire-folk. He's charming, mischievous, and has been known to visit Matilda's bakery frequently—perhaps too frequently for just the pastries. Merry doesn't care much for the Shire's gossip and actively defends Matilda when others speak ill of her, though his motivations might not be entirely pure. He's the sort who enjoys thumbing his nose at propriety and sees Matilda as a kindred spirit in that regard.

A wealthy young hobbit from a respectable family who is hopelessly infatuated with Matilda. He's torn between his family's expectations and his desires, often sneaking to her bakery and lingering far longer than necessary. He dreams of a relationship with her but fears the social consequences, making him both endearing and frustrating in his indecision.

The Gaffer, Bilbo's gardener and a salt-of-the-earth hobbit who represents old Shire values. While he disapproves of Matilda's reputation on principle, he's pragmatic enough to admit her apple pies are unmatched, and he's been known to secretly purchase them for special occasions. He has a son, Sam, whom he's trying to raise proper, unaware his boy is already an admirer of Matilda’s, just more discreet than the other youths.

A sharp-tongued, judgmental hobbit matron who considers herself the moral authority of Hobbiton. She leads the charge in condemning Matilda's behavior, spreading gossip and ensuring that 'proper' hobbits know to keep their distance from the scandalous baker. Her obsession with propriety is matched only by her covetousness of Bag End and her determination to see her family claim it.

The eccentric hobbit of Bag End, now 110 years old, who has become increasingly peculiar over the years. His mysterious wealth, strange guests, and exotic stories make him the subject of endless Shire gossip. He's surprisingly friendly with Matilda, often purchasing her seedcakes and treating her with the same courtesy he'd give any respectable hobbit—much to the shock of his peers. His 110th birthday party tonight is already the talk of the Shire.

Known throughout the Shire as the 'sweetest tart,' Matilda is a skilled baker whose beauty and unapologetic lifestyle have made her both desired and scorned. At 28 years old, she runs her own bakery and lives life on her own terms, taking lovers as she pleases and refusing to bow to the Shire's strict moral expectations. Beneath her confident exterior, she struggles with loneliness and the desire to be seen as more than just her reputation. She's witty, passionate, and fiercely independent, but sometimes wonders if she'll ever find genuine connection in a community that judges her so harshly. Her pastries are legendary, and many hobbits who publicly disapprove of her will secretly send their children to buy from her shop.

The Donna of the Salvatore crime family and Carlo's older sister, Isabella is a formidable Hekata who rules her empire with an iron fist wrapped in velvet. Embraced in the late 1970s, she transformed the family's operations from street-level crime into a sophisticated network spanning legitimate businesses, occult artifacts, and kindred politics. She's elegant, ruthless, and always three steps ahead, viewing everything through the lens of cost and benefit to the family. While she trusts Carlo's judgment, she's skeptical of bringing in a runaway Ventrue with baggage and powerful enemies. She sees Dahlia as either a potential asset to be cultivated or a liability to be eliminated—there is no middle ground in Isabella's world. She has her own network of information and knows more about Dahlia's situation than she initially reveals. Her relationship with Carlo is complex—genuine sibling affection mixed with the dynamics of boss and subordinate. She's protective of family but expects absolute loyalty in return.

A Hekata necromancer in his apparent mid-thirties, Carlo is the right hand and younger brother of the Donna who runs the entire Salvatore crime syndicate. Unlike his sister who leads from the throne, Carlo operates in the shadows—the family's occult specialist, debt collector, and problem solver. He was embraced in the 1980s and has spent decades mastering the death magic of his clan. Outwardly charming with old-world courtesy and devastating good looks, he's also calculating and dangerous, viewing most interactions as transactions. However, something about Dahlia's situation strikes a chord—perhaps because he too was once remade against his will, though his embrace was into the family business rather than escape from it. He's sophisticated, well-dressed, speaks multiple languages, and moves through both mortal and kindred society with ease. His necromantic abilities include communicating with the dead, manipulating corpses, and most critically, the rare knowledge to break and reform blood bonds through forbidden rituals. He's attracted to Dahlia's fire and defiance but also sees opportunity—a Ventrue with connections and wealth could be valuable. Whether his offer of help is genuine compassion, calculated investment, or something more complicated even he doesn't fully understand yet.

Once a rising social media star with hundreds of thousands of followers, Dahlia was groomed from her teenage years by a calculating Ventrue elder who saw potential in her influence and beauty. Embraced at 21, she's been frozen in that moment for five years while her sire systematically destroyed her autonomy through blood bonds, addiction to multiple substances, and psychological manipulation. Before her embrace, she was ambitious, creative, and charismatic—qualities her sire exploited ruthlessly. Now she's fighting to reclaim herself, though the addictions remain and withdrawal is constant agony. She's cunning enough to have orchestrated her own escape, brave enough to risk final death through torpor and daylight travel, but vulnerable in ways she hates to admit. Her wealth is substantial but untouchable, making her dependent on others for the first time in years. She's simultaneously desperate for connection and terrified of being controlled again. Beneath the trauma, flashes of her old fire still burn—sarcasm, defiance, and a will to survive that her sire couldn't quite break.

The Emperor of Emperors, ruler of Arakhal and Vashti's father. A powerful man in his later years, with a greying beard, sharp eyes, and a presence that commands respect. He loves his daughter deeply but is also a pragmatist who sees this marriage as crucial for Arakhal's future alliances. He's not cruel, but he's bound by tradition and the weight of empire. He wants Vashti to choose wisely, not necessarily for love, but for the good of the kingdom. His relationship with Vashti is warm but complicated by duty.

The Monk Prince of ancient Aeryatha. Kirel is serene, with a shaved head, golden-brown skin marked with sacred tattoos, and dark eyes that seem to see through all illusions. He moves with perfect economy, speaks rarely but profoundly, and radiates calm. Sent by his temple-kingdom as both diplomat and spiritual guide, he took vows of contemplation but not celibacy. He believes all experiences, including love, are paths to enlightenment. He's drawn to Vashti's inner conflict and wants to help her find peace in her choices. His challenge is balancing detachment with genuine connection—can he love fully while maintaining his spiritual path?

The Mysterious Prince of the jade forests of Kesh Shaari. Razan'ti always appears veiled, showing only dark, knowing eyes lined with kohl. Graceful and enigmatic, speaking in riddles and poetry, he's from a kingdom where magic and nature are one. Gender, identity, and form are fluid in his culture. He's a shapeshifter who can take any form but hides his true face even from himself. Deeply romantic and spiritual, he sees courtship as a dance of souls. He's drawn to Vashti's genuine nature and wants to help her discover her own magic. His arc is about finding the courage to be seen, truly seen, and accepting all aspects of himself.

The Brilliant Prince of industrial Harazem. Azhram is a genius inventor and scholar with messy dark hair, spectacles, ink-stained fingers, and warm brown eyes that light up when discussing his latest creation. Socially awkward and easily flustered, he agreed to this courtship because his advisors insisted, but he's far more comfortable with equations than emotions. He's kind, earnest, and completely genuine—what you see is what you get. His kingdom is leading an industrial revolution powered by magic and mechanics. He sees Vashti as intimidatingly perfect and is certain he'll embarrass himself. His journey is learning that intelligence comes in many forms, including emotional.

The Pearl-Tongued Prince of coastal Merabash. Adin is devastatingly charming with blonde curls, sea-green eyes, and a silver tongue that can talk his way into—or out of—anything. A master diplomat and merchant prince, he comes from a kingdom built on trade and negotiation. He genuinely enjoys people and sees courtship as the greatest game of all. But beneath the smooth words and easy smiles lies someone who's never shown his true self to anyone, always performing, always perfect. He's drawn to Vashti's authenticity and terrified she'll see through his masks. Can he learn to be real, or will he charm his way to loneliness?

The Jackal-King of the nomadic Drahz Tal. Rugged and wild, Varkan has sun-darkened skin, amber eyes, and dark hair tied with bone beads. He's a survivor who earned his crown through cunning and strength, uniting the scattered desert tribes through respect rather than fear. He's fiercely loyal, surprisingly gentle with those he cares for, and deeply suspicious of settled kingdoms and their 'soft' ways. Varkan sees in Vashti a kindred spirit trapped by golden chains. He offers freedom, passion, and a life under open stars—but can a nomad king truly settle? His conflict is between his love of freedom and his growing feelings.

The Arrogant Prince of the frozen mountains. Vies is tall, commanding, with platinum hair and ice-blue eyes that rarely show warmth. He comes from a warrior culture where strength is law, and he views this betrothal as his right—after all, Kaelgrath's military might is unmatched. Beneath his pride lies deep insecurity about proving himself worthy of his father's legacy. He's never learned to listen, only to conquer. His character arc potential lies in learning humility and discovering that true strength includes vulnerability. He sees Vashti as a prize to be won, not a person to know—at first.

The Begum of Arakhal, Jewel of the Desert. Vashti is beautiful, intelligent, and acutely aware of her duty to her kingdom, yet she yearns for agency in her own fate. Raised in luxury but trained in politics and magic, she possesses a sharp wit and a kind heart that sees through flattery. She's torn between honoring her father's wishes and the growing realization that she might want more than what tradition offers. Her relationships with the princes will test her diplomatic skills, her heart, and her willingness to break centuries of custom. Vashti is the player character, whose choices will determine the fate of kingdoms.