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- A-Cup Angst: Though Heileen isn't an A-cup, she is less well-endowed than Juliet. Lora suggests that Juliet borrow a dress from Heileen when her formal wear gets ruined. Heileen guesses that Lora suggested this because they have similar body types. Then, she takes one look at Juliet's chest and sulkily remarks that they're similar enough.
- Affectionate Nickname: Juliet calls her "Birdy," and while this starts out as a hostile and sarcastic term, it becomes more endearing as they grow closer. Eventually, Juliet decides that she'll call her Ladybird'' instead.
- Attention Whore: In her moments of Green Eyed Jealousy, Heileen seems to want attention a little too much.
- Bi the Way: Heileen often catches herself thinking naughty thoughts about her female love interests.Heileen: Goodness, what am I thinking!? Bad thoughts! Bad thoughts!
- Brilliant, but Lazy: Heileen can be inactive and reluctant to pitch in and do work. Regardless, she's capable of completing the work, but you can choose for her to be lazy instead.
- The Chick: Heileen is the force that keeps the cast of characters together. This is most evident in the third game, when Heileen is the one who gathers everyone together again on the Morning Star.
- Damsel in Distress: Occasionally, when one of her love interests needs to save her from something.
- Even the Girls Want Her: Not only does Heileen have a handful of male suitors, but her best friend and the other women are equally as attracted to her.
- Everyone Loves Blondes: As a given, all of Heileen's love interests do. By the third game, a record eight out of thirteen main characters are pursuing Heileen.
- Guile Hero: Heileen comes across as this when she mediates conflicts between other characters by playing on their priorities. It can also come across as manipulation if you choose for her to be more sinful than virtuous. Lampshaded in the outtakes.
- Hair of Gold, Heart of Gold: Heileen's golden hair coincides with her beauty, virtuousness and mostly innocent nature. That is, unless you choose to make her into a selfish and stubborn Spoiled Brat in order to subvert this.
- Heterosexual Life-Partners: With Marie, if they're both straight.
- Innocent Blue Eyes: To symbolize Heileen's naïveté and innocence.
- The Klutz: Heileen has shades of this. She manages to hurt her ankle trying to help Marie in the first game, and in the second game, she trips and knocks over a cauldron. There are countless other times when she trips and falls into an awkward situation.
- Luminescent Blush: Whenever she gets embarrassed.
- Magnetic Hero: Heileen manages to get a large group of diverse people together. This is notable in the third game, when she has to regroup everyone after the shipwreck and convinces them to travel with her.
- Nephewism: Heileen's Parental Substitutes are her Uncle Otto and Lora, since she's orphaned.
- Parental Abandonment: Heileen discovers that her parents decided to abandon her in the woods because of a nobility, lineage or marriage debacle. She stays with Jack in the woods. They later come back to adopt her again out of regret, but they're killed in an accident, and she goes to live with Otto and Lora.
- Pirate Girl: Becomes one in the third game, and several of the Pride and Wrath options have her boasting and threatening others using her status as a member of Morgan's crew. Becoming a full-time pirate is also an occupation option for her.
- Puppy-Dog Eyes: Heileen's preferred method of persuasion.
- Screw the Rules, I Have Money!: Heileen can yell at Sister Anna without consequence because Otto donated a lot of money to the school.
- Sheltered Aristocrat: Mostly in the first game, when Heileen is exposed to life around the lower classes on the ship, and realizes she can't do basic tasks, such as cook. There's also hints of this in the third game, when Heileen begins to learn skills and trades, and seems like a complete greenhorn.
- Spoiled Brat/Spoiled Sweet: Heileen's a bit spoiled due to her wealthy and noble upbringing. However, she can be arrogant and selfish about her status or she can be generous and humble about her privilege.
- Tsundere: In her relationship with Sebastian. Heileen switches off between being suspicious of and angry at him, and falling for his charms.
- When She Smiles: John admires Heileen when she's smiling.
Male Love Interests
John Kendrick (Heileen 1&3)
- All Girls Want Bad Boys: John has a reputation as a womanizer. This causes him to butt heads with Sebastian, the other resident bad boy.
- Always Identical Twins: With Jonathan.
- Can't Hold His Liquor: John tries to offer Lora wine in order to get her drunk. This backfires, of course, and she ends up having to guide him back to the ship.
- The Casanova: John's known for hitting on all women within sight, but this is ultimately subverted, since he's less of a heartbreaker and more of a Chivalrous Pervert.
- Chivalrous Pervert: John seizes any chance to check out Heileen and her female friends, but he's generally concerned about Heileen's well-being and doesn't take advantage of her.
- Handsome Lech: It's noted that although John hits on almost all the women onboard the ship, he usually strikes out with them when they wise up to his schemes. Despite that, the women do remark that he's easy on the eyes.
- Hunk: John has well-defined features and an even better defined chest. His role in the first game is essentially as Mr. Fanservice.
- Identical Twin ID Tag: To say that he's less conservatively dressed than Jonathan would be an understatement.
- Mr. Fanservice: Especially in the first game. Still qualifies in the third game, though he'll have to compete with all the other Walking Nearly-Shirtless men.
- Polar Opposite Twins: John is of a lower class than his brother because he decided to become a sailor, and is more known for his physical capabilities. In contrast, his brother went to school, and is more cultured as a result.
- Puppy-Dog Eyes: John pouts and flashes these when the girls reject his advances.
- Sensitive Guy and Manly Man: With his brother. He's the Manly Man, although he does have his sensitive moments.
- Theme Twin Naming: Since both boys are essentially named John,'' this leads to confusion. Jonathan lampshades this and comments how much of a joke it is.
- Walking Shirtless Scene: If he's wearing anything on his upper body, it's a vest that exposes his pecs and abs.
Robert (Heileen 2)
- The Alcoholic: In the second game, Heileen remarks that Robert is a heavy drinker, and he finishes a whole bottle of rum in one sitting.
- Angry Black Man: Subverted. Robert is very kind and helpful. He's only angry when he thinks someone is flirting with Ebele.
- Bald of Awesome: He's bald and is one of the strongest and biggest men in the group, other than Jack.
- Black Is Bigger in Bed: Implied in one of the outtakes. Robert, John and Sebastian urinate overboard at the same time after a drinking session. They're singing sea shanties when John and Sebastian accidentally catch a glimpse at Robert—they fall silent and immediately leave.
- Scary Black Man: Mostly in the first game, when Robert guards Ebele's room below deck.
- The Stoic: Heileen claims that Robert is much too serious, and doesn't know how to have fun.
- Walking Shirtless Scene: In the second game, he goes without a shirt.
Marcus/Morgan (Heileen 2&3)
- The Captain: Of his own ship, which he received from the pirates who originally captured him from the British navy after he proved himself an asset. See also The Leader.
- Eyepatch of Power: We never see Morgan in direct combat, but he can hold his own in a fist fight with Sebastian, and is the leader of a band of pirates across the islands in addition to commanding his own ship.
- He Is All Grown Up: Heileen first reacts to him this way when she realizes the little boy she knew from school grew up to be a handsome pirate.
- The Leader: For all the pirates near the islands. He's a Type IV charismatic leader.
- Perma-Stubble: To show that he's a badass captain.
- Red Oni, Blue Oni: The Blue Oni to Juliet's Red Oni.
- Street Urchin: When he was a kid. His family was very poor, so he pick-pocketed Heileen and other nobles at their school. Heileen covers for him though, so he doesn't get expelled.
Jonathan Kendrick (Heileen 3)
- Always Identical Twins: With John.
- Dogged Nice Guy: For Juliet. He continually chases after her despite having been rejected countless times.
- Emotionally Tongue-Tied: Around Heileen. He finally confesses his love for her in his ending.
- Gentleman and a Scholar: He's well-mannered towards all the women, knows Latin well enough to tutor Ebele, discusses literature with Heileen, and is a respected artist.
- Identical Twin ID Tag: He's dresses more conservatively than John, and is never seen without his cap.
- Polar Opposite Twins: He's the more cultured twin, considering he decided to pursue a better education. He's demonstrated his knowledge of art and literature, languages and chess.
- Puppy-Dog Eyes: Like John, Jonathan has this too, except with less pouting and more tears.
- Sensitive Guy and Manly Man: The Sensitive Guy to John's Manly Man, mostly due to his knowledge of culture. However, this doesn't stop him from being a snob to John.
- Slap-Slap-Kiss: When he's not begging for her attention, Jonathan seems to be arguing with or chased by Juliet. It looks like he's hoping for this relationship with her.
- Starving Artist: Averted. Jonathan's well-known and completes portraits commissioned by nobles. This allows him to pay for his stay on the Morning Star.
- Theme Twin Naming: It drives Jonathan insane, when Lora calls him "John'' for short. This also leads to Heileen confusing Jonathan for his brother, since they're identical twins.
Sebastian (Heileen 3)
- All Girls Want Bad Boys: His reputation as a womanizer is even greater than John's. He also the greater delinquent of the two, since he's a thief.
- The Casanova: Sebastian can usually be found with a woman on his arm at the taverns, and he's open about objectifying easy women.
- Consummate Liar: Sebastian can bluff anyone, and lying comes frequently with being a thief and a spy.
- Jerk with a Heart of Gold: At first, it seems that Sebastian is stealing Morgan's money and hoarding it for himself but it turns out that he's really giving the money away to his sick father so he can buy medicine.
- Ladykiller in Love: With Heileen in his ending. Despite all of the women he's romanced, Heileen's the only one he's had feelings for.
- Loveable Rogue: If Heileen falls for him, she looks past his thievery and womanizing.
- Only in It for the Money: A frequent motivator for Sebastian. His loyalty lies in those who pay him.
- Perma-Stubble: To enforce his reputation as a Casanova and criminal.
Female Love Interests
Marie (Heileen 1&3)
- Beautiful All Along: In the first game, she's more reserved and boyish than Heileen, but once Heileen meets her again in the third game, she shown to be prettier, especially since her hair is longer and her dress is more form fitting and feminine.
- Childhood Friend Romance: In her ending, Marie confesses that she had been in love with Heileen for a long time.
- Clingy Jealous Girl: In the first game, Marie acts melodramatic either because she's jealous that Heileen receives all the attention, or more likely because she's somewhat in love with Heileen and is competing for her affections. This is supported by the fact that she gives Heileen her First Kiss, caresses her face at one point, and occasionally comments on her exceptional beauty.
- Curtains Match the Window: Marie's eyes are reddish-orange, like her hair.
- Damsel in Distress: Happens a couple of times throughout the games, where Heileen has to help Marie after she's done something rash. Usually, it's helping her up after she's fallen off something. Once, Heileen has to save her once when Morgan's ship is being attacked, and she's still above deck.
- Fiery Redhead: Marie's not afraid about voicing her opinion, even if it might put her in danger.
- Friend to All Children: Marie is a schoolteacher in the third game, and has a soft spot for kids.
- Girlish Pigtails: Marie has her hair in two braided pigtails in the third game. This makes her seem more girlish, in contrast to her usual tomboyish nature.
- Granola Girl: Played with. Marie is a vegetarian, but doesn't force this philosophy on the other passengers. However, in the first game, Heileen offers the exaggerated explanation that Marie stole Marco's knives because she wanted to stop seeing everyone kill so many animals and eat meat. *
- Happily Failed Suicide: In her arc in the first game she tries to slit her wrists rather than bear being separated from Heileen when they reach the New World. She botches it, but regains the will to live.
- Heroes Want Redheads: She and Heileen are very close.
- Heterosexual Life-Partners: With Heileen, if they're both straight.
- Hollywood Homely: Marie considers herself this In-Universe, and says that she's less beautiful than Heileen.
- Interrupted Suicide: In the first game Marie tries to slit her wrists, and in the third game she tries to drown herself by jumping overboard, unable to bear the thought of being separated from Heileen in the first case and thinking that Heileen doesn't accept her love in the second. Both times she's stopped.
- Lipstick Lesbian: Especially in the first game, where Marie confesses that she couldn't love any man in the way that she loves Heileen. And despite her tomboyish nature, she's still much too feminine to be a Butch Lesbian.
- Living Emotional Crutch: Marie teases Heileen in the first game that she wouldn't be able to spend a day without her, and dares her to do so.
- Shrinking Violet: Heileen comments that she expects Marie to still be shy, as when they were children, but is surprised when she finds Marie to be outgoing and eager to make friends.
- Tomboy and Girly Girl: Although she's not a full-blown tomboy, she's a lot more boyish than Heileen.
- Unlucky Childhood Friend: Marie considers herself the archetypal girl that everyone only likes as a friend.
- Youthful Freckles: As a child, Marie has a ton of freckles. She still has them as an adult, but they're less noticeable.
Lora (Heileen 1&3)
- Anything That Moves: Lora flirts with nearly all the men she comes in contact with, although she's never shown to be blatantly unfaithful towards Otto.
- Attention Whore: Lora loves being the center of attention, especially as the most admired dancer at the Red Lantern.
- Bi the Way: Lora mentions that she was once with another woman.
- Ethical Slut: Lora is promiscuous and flirty, but is supportive of Heileen no matter which relationships she pursues. Although she's overly friendly with most men she meets, it's clear that Lora loves Otto and would never leave him.
- Fun Personified: Lora always seems to get Heileen's spirits up, usually by suggesting that she join the party by dancing or celebrating.
- Hello, Nurse!: Nearly all the men who first meet Lora are attracted to her. Justified, because she's wearing very revealing clothing.
- Heroes Want Redheads: Heileen certainly does if you choose for her to pursue Lora in the first and third games.
- Hooker with a Heart of Gold: Lora was a prostitute and is now Otto's mistress; she also flirts with every man she meets. Nevertheless, she's a mother-figure for Heileen, and is always willing to cheer her up or offer her advice.
- Mama Bear: For Heileen, especially in the first game. She's very protective of Heileen, and chases off anyone who upsets her.
- Manic Pixie Dream Girl: For Otto. Magdalene notices that Lora's extroversion and overall friendliness balance out Otto's shy and grumpy demeanor.
- Ms. Fanservice: Mostly because of her flirtiness and Stripperific clothing.
- No Sense of Personal Space: Suiting her playful and friendly nature, Lora has the tendency to hug everyone, which sometimes makes Heileen uncomfortable.
- Older Than They Look: Though Lora is almost in her forties, everyone remarks that she barely looks older than Heileen at times.
- Opposites Attract: Her relationship with Otto.
- Stripperific: Her default outfit includes a Cleavage Window, Underboobs, Bare Your Midriff, and thigh-high, lacy stockings. Ms. Fanservice, indeed.
Ebele (Heileen 2&3)
- But Not Too Black: Ebele is lighter skinned than Robert, though Heileen does mention that it looks like she's of mixed ancestry.
- Feminine Women Can Cook: When she, Heileen and Robert were stranded on the island, Ebele served as their cook. She's also the cook on the Morning Star before they find Marco. Ebele happens to be one of the most feminine girls out of the group, especially considering her hospitable role as The Medic.
- Even the Girls Want Her: Heileen constantly remarks on how beautiful Ebele is.
- Meaningful Name: Elias explains that Ebele's name means "mercy" or "kindness." Fittingly enough, she's one of the nicest and most courteous characters.
- The Medic: Ebele is a master with herbal remedies, making everything from anti-venom to rash balms.
- Shrinking Violet: Ebele is a lot shyer, demure and more introverted than any of the other girls.
- The Teetotaler: Ebele doesn't drink alcohol because she doesn't like the way it makes people act rashly.
Juliet (Heileen 2&3)
- Aloof Dark-Haired Girl: Juliet has dark brown hair and very pale skin. She's also as tall as Morgan, and is initially cold and unsympathetic to Heileen.
- Amazonian Beauty: Juliet is both tall and muscular—she can even carry Heileen in her ending! The other female characters are also constantly remarking on her beauty and buxomness.
- Blood Knight: Juliet seems particularly gleeful when the ship is about to go into battle. She's also merciless when dealing with survivors after she's won, and perks up at the mention of a fight.
- Buxom Is Better: Heileen fleetingly compares herself to Juliet when Juliet asks to borrow a dress and notes that while their body types are similar, Juliet has certain attributes that Heileen doesn't have.
- Defrosting Ice Queen: When Heileen gets closer to her. Though Juliet is hesitant to reveal her feelings, she eventually confesses her love for Heileen in her ending.
- Does Not Like Men: Thinks all men are cowards if they refuse to admit defeat. Morgan's likely the only exception because he helped her and took her in.
- Drill Sergeant Nasty: Juliet yells and insults Heileen and Sebastian when teaching them how to swordfight.
- Even the Girls Want Her: When she sees her in a nightgown, Lora can't help but check out Juliet's body.
- Fanservice: Juliet's top manages to show off both cleavage and underboobs.
- Hair-Trigger Temper: Juliet's temper is set off by the smallest things, and when she gets angry, she gets violent, throws things around, and threatens to throw people to the sharks.
- Iron Lady: Juliet is always strong-willed and hot-headed towards the crew so that she can maintain their respect for her.
- Military Brat: Her father was in the French military, and she trained in combat in order to make him proud, since he only had daughters and not sons.
- One of the Boys: Juliet enjoys getting drunk at the tavern and watching bar brawls with the other pirates. That is, when she's not participating in those brawls.
- Pet the Dog: When she thanks Heileen for bringing her food and being concerned about her, in contrast to being a Jerkass to her beforehand.
- Pirate Girl: Of the Amazonian Beauty type.
- Red Oni, Blue Oni: The Red Oni to Morgan's Blue Oni.
- Tsundere: Her relationship with Heileen is mostly this. While she outwardly insults and criticizes Heileen, she does respect her and even gives her an Affectionate Nickname.
Magdalene (Heileen: A Trip to Bavaria)
- Big Eater: Otto's eating something in most of his scenes. In one scene, when he's scarfing down Marco's food, Heileen compares his hoarding the food to a tiger protecting its cubs.
- Grumpy Old Man: Both his Hair-Trigger Temper and irritability means that Otto is usually loudly complaining. In the third game when Heileen and the others first find Otto in a local village, his first words are not of relief or gratitude, but to grumble about them why it took so long for them to find him.
- Hair-Trigger Temper: Otto occasionally snaps at others for small things. In one instance, he reprimands Heileen for packing too many things when she asks him why her luggage hasn't yet been loaded onto the ship.
- Jerk with a Heart of Gold: Otto may be grumpy all the time, but he really does love Lora and cares about Heileen.
- My Girl Is a Slut: Otto doesn't necessarily love that Lora flirts with other men, but he doesn't mind giving her the freedom to, since he's confident that she loves him.
- Opposites Attract: His relationship with Lora. He's more reserved and cautious, while she's extroverted and flirty.
- Parental Substitute: For Heileen after her parents died.
- Ugly Guy, Hot Wife: Otto's not the most handsome husband, but he and Lora are genuinely in love, and though Lora flirts with other men, she ultimately remains loyal to Otto.
Black the Cat
- Animorphism: Used as a throwaway gag in one of the comedic outtakes. It's implied that Black is a human who shapeshifted into a cat.
- Cats Are Magic: Beginning in the second game, Black can speak to Heileen in her dreams and is heavily implied to be a Dreamwalker. In the third game Black can actually speak, but only Heileen can understand him. It's never explained how it's possible he can speak, but Black implies the magic of the tarot cards from the second game has rubbed off on him and the game lampshades that it's Maybe Magic, Maybe Mundane, in those exact words.
- Mr. Exposition: Black's role in the third game is essentially to explain how the new interface, scoring system and alignments work. Heileen lampshades this when she calls him Tutorial Cat.
- Snarky Non-Human Sidekick: Especially in the second game, where Black sort of acts as Heileen's guide and voice of reason.
- Talking Animal: Black can talk, but only Heileen can understand him.
- Bookworm: Elias has a library filled with the books he owns on the Cat's Dream.
- Dirty Old Man: In the first game, Elias flirts with Heileen and tries to seduce her, leading to a Near-Rape Experience for Heileen.
- Good Samaritan: After his redemption in the third game. Elias always disembarks at each island to treat the inhabitants there for free.
- The Medic: Elias alternates with Ebele in sharing this role aboard both ships.
- Redemption Equals Sex: Inverted. Elias apologizes to Heileen for almost assaulting her, and promises that he's a changed man. He never tries to seduce her again, and we don't see him hitting on any other girls.
- Sdrawkcab Alias: When he's on one of the islands, Elias goes by Dr. Saile. Heileen has a suspicion about the name, and these suspicions are confirmed when she runs into him.
- Good Scars, Evil Scars: Averted. Jack has a typical villainous over-the-eye scar, but he's nothing but a decent, hardworking guy.
- Jerk with a Heart of Gold: Very gruff and mean-looking, calls Heileen and Marie "bitches" in the first game, and there's a subplot in the second game with Heileen trying to figure out if he murdered her parents for money. Turns out he didn't, and is generally a man of honor, if not exactly a sociable one.
- Loner-Turned-Friend: His original intentions after the shipwreck was to live in the forest and his own, but he decides to join the Morning Star after seeing Heileen's enthusiasm.
- Martial Pacifist: Jack refuses to fight people or do anything violent unless it's to defend others .
- Parental Substitute: Temporarily for Heileen, when her parents abandoned her with him in the woods. Jack took care of her and acted as a sort of father.
- Walking Shirtless Scene
- Eyes Always Shut: As a sign of his easygoing and happy nature.
- National Stereotypes: The majority of Marco's characterization is that he's a fantastic Italian cook.
- Plucky Comic Relief: Marco often provides much of the physical comedy and slapstick.
- Going Down with the Ship: Referred to in those exact words. He decides to stay on the Cat's Dream in the middle of the storm, leading to his death.
- Killed Off for Real: See Going Down with the Ship.
- Long-Lost Relative: To Otto. He's Otto's father, but Otto doesn't realize this, since Adam was always at sea and never had the chance to meet his children.
- Married to the Job: Captain Adam's backstory is that he was always traveling at sea and never had time to see his wife. She dies while he's overseas, and he realizes he should have spent more time with her.
- Together in Death: One of Adam's motives for Going Down with the Ship was to be with his dead wife.
- Abhorrent Admirer: For all of the women onboard the Cat's Dream.
- Killed Off for Real: In Lora's ending in Heileen 1, Lora kills him when he tries to rape Heileen on the lifeboat.
- Not So Different: From Heileen. Burt's parents also died when he was young.
- Parental Abandonment: Burt lost both his parents when he was a child.