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Visual Novel / Heileen

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Heileen is a Ren'Py-based visual novel trilogy created by Tycoon Games/Winter Wolves about Heileen, a noble girl living in 17th century England. The series focuses on the developing relationships between Heileen and the other characters in addition to Heileen's maturation from a naïve, self-centered girl into a responsible young woman.

In Heileen 1: Sail Away (2008), Heileen reluctantly leaves her happy, normal life in Liverpool on a voyage to the New World with her grouchy Uncle Otto and his mistress, Lora. Joining Heileen on her journey are Marie, her childhood best friend, and John, the attractive sailor Heileen has a crush on. During the voyage, Heileen stumbles into personal drama surrounding her friends and family, receives her first kiss, and uncovers a mystery on the ship.

In between the first and second game, the freeware flash game Heileen: A Trip to Bavaria (2009) was released. The game is a prequel to Heileen 1: Sail Away, and features Heileen's trip to Bavaria on her 16th birthday. Heileen meets and befriends Magdalene, a humble farmer. Heileen must leave for the New World, but Magdalene tries to convince her to stay. You can play the game at the Tycoon Games website.

Heileen 2: The Hands of Fate (2009) leaves Heileen shipwrecked on a deserted island with Robert and Ebele. Amidst searching for other survivors from the wreckage, Heileen must discover a way off the island. Heileen finds a mystical deck of tarot cards representing the Seven Heavenly Virtues and Seven Deadly Sins. The tarot cards prompt flashbacks to her life and childhood back in England, in which Heileen must make key choices establishing life lessons she has learned. The cards can alter her past and generate items in the present according to Heileen's choices. Although the second game did not originally include voices, a voiced version was later released in 2010.

In the final installment, Heileen 3: New Horizons (2012), Morgan, an infamous pirate, and his crew rescue Heileen from the island. Heileen agrees to work on the ship in exchange for a chance to travel to the various nearby islands to search for her friends. By the conclusion of this game, Heileen must choose which profession she will go into. The expansion, Heileen 3: Sea Maidens (2013), added four yuri romances to the existing four het romances.

While the first two games offer a point-based system dependent upon the quests Heileen completes, the third game gets rid of this system and introduces a Raising Sim format in which Heileen learns skills that eventually lead her into a trade. Regardless, the focus in the series lies on the variety of endings and relationships you can get. The games can be downloaded from the Winter Wolves website. Free demos are also available for all three games.

Heileen provides examples of:

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    Tropes Present throughout the Series 
  • Animesque: The art style has a very manga flavor to it.
  • Beauty Contest
    • In the second game, Heileen participates in the Duke of Liverpool's beauty contest for young girls.
    • In the third game, the pirates and passengers on the Morning Star participate in a casual beauty contest to decide whether Lora, Heileen, or Ebele is the prettiest of the three. Ebele wins, since John was the tiebreaker, and couldn't choose between Heileen and Lora.
  • Bridal Carry
    • Robert's scene in the second game. He carries Heileen this way after she hurts her ankle.
    • Juliet's ending in the third game. She carries an injured Heileen back to the ship.
  • Captured by Cannibals
    • In Heileen 2, Heileen and Ebele discuss this trope after they're captured by island natives. They trick the natives and run away before anything else happens.
    • In Heileen 3, Heileen and the others believe this will be played straight when they visit a local village, but it's ultimately subverted. The local tribe leader speaks English, and while the natives are hesitant to welcome the visitors at first, they leave them alone once they see that they're only there to provide medical aid.
  • Character Development: Though the story mainly focuses on Heileen's development, the other characters develop throughout the series as well. See also Hidden Depths and Coming of Age Story.
  • Character Title: The main character's name is Heileen.
  • Comic-Book Time: Played with: According to the third game, the events of The Hands of Fate take place over almost a year. In New Horizons, it's stated that several years have passed since the shipwreck at the end of Sail Away happened.
  • Coming of Age Story: The series centers on Heileen's Character Development from a young girl into a young woman. This includes receiving her First Kiss, exploring her sexual preferences, learning skills and trades, and ultimately, falling in love.
  • Continuity Nod
    • In the first game, Lora offhandedly mentions that she gives Otto “special massages.'' We assume that this means sex, but in the third game, we see her give Marie an actual massage that is both pleasurable and relaxing.
    • In the second game, we learn that Heileen's Trademark Favorite Food is milk and biscuits. This later comes back in the third game, when Lora mentions that she remembered this about Heileen.
  • Driving Question
    • Heileen 1: Who or what is “Ebele,'' and how are Lora and Otto involved?
    • Heileen 2: How did Heileen's parents die, and how can they get off the island?
  • Exact Eavesdropping: Whenever Heileen eavesdrops on the other characters (which is often) she always overhears juicy tidbits about their love lives or other useful gossip.
  • Fake-Out Make-Out
    • In Heileen 1, John pretends to kiss Heileen when Elias walks in on them snooping in his library.
    • In Heileen 3, Sebastian pretends to make out with Heileen when they're almost caught by the pirates they're tailing. Heileen can then choose to make out for real.
  • Fanservice: There's something for everyone! While Lora is undoubtedly Ms. Fanservice, almost all characters show a good amount of skin. Women have the chance to show off in skimpy clothing, and men occasionally walk around shirtless, if this isn't already their default outfit.
  • Forgotten First Meeting
    • Heileen's shocked to hear that she's met Jonathan before, when he was completing Lora's portrait back in Liverpool.
    • When she first meets Morgan, Heileen doesn't realize that he's Marcus all grown up.
  • Gay Option: Four total across all three games: Marie, Lora, Ebele, and Juliet.
  • Genre Shift: A small one. While the first and second games include some sort of mystery plot, the games gradually focus more on Character Development and the romances.
  • Green-Eyed Monster: Plays a huge part in the games. Heileen is typically jealous when her love interests pay more attention to other people, even if it's hypocritical when she's romancing everyone in the games. Additionally, in the third game, your love interests will get jealous if your relationship score with a certain person is high enough—you're forced to choose between the two people arguing over Heileen.
  • Guide Dang It!: Although there are two lesbian endings in the first game, they're much more difficult to get than John's ending, which is the default. You also might need to consult guides for the second and third games in order to get each character's CG/ending.
  • Hidden Depths
  • Interrupted Suicide
    • Played straight when Marie tries to commit suicide by cutting her wrists—Lora stops her in time.
      • If pursued romantically in the third game, Marie throws herself overboard in a fit of despair, thinking Heileen would never accept her feelings.
    • Played with when Heileen tries this when she sees Sebastian jumping off a tall cliff into a lake. He jumps into the lake before she can stop him…then, she realizes he wasn't committing suicide; he was just diving.
  • Kiss of Life
    • Marco tries to invoke this at the end of Heileen 1 when he pretends to need mouth-to-mouth resuscitation from Heileen. Heileen catches on, and shocks him into ending the charade when she suggests Jack do it instead.
    • John also tries to invoke this by pretending to pass out on the raft, so that one of the girls will resuscitate him. In one choice, Heileen wises on to this and suggests that it would be better for Robert to give John mouth to mouth.
    • Finally played straight in Sebastian's ending when he revives Heileen after she almost drowns.
  • Leave the Two Lovebirds Alone
    • In the first game, Marco and Marie leave the party so that only John and Heileen are left. John discusses this trope when he says that he plans on taking advantage of being alone with Heileen so that he can seduce her.
    • In the third game, Lora drags Otto away from the ship's deck so that Morgan and Heileen can have alone time.
  • Lost at Sea
    • Marie's ending in the first game has Marie and Heileen adrift on a raft until they reach land.
    • In Heileen 3, Heileen, Ebele and Juliet find John adrift at sea on a raft.
  • Love at First Sight
    • In a diary entry, Jonathan claims that he fell in love with Heileen the first time he saw her.
    • In Sebastian's ending, both he and Heileen claim they fell in love when they first met.
  • Love Triangle: Possible in all three games if you choose to play the field, but most notable in the third game, where you have to face the consequences. In the third game, certain romances will conflict with other romances if both relationship values are high enough. For instance, if Heileen romances both John and Jonathan, she'll need to side with one guy in one encounter. If she sides with John, she loses relationship points with Jonathan, and vice versa. Since you essentially need to maximize relationship points with a character in order to get their ending—and thus, must almost always choose the option that allows you to gain points with them in choice encounters—this means that you need to choose one of the men instead of trying to romance both.
  • May–December Romance
    • Lora and Heileen. Lora is twice Heileen's age. In the first game, Heileen is 18, while Lora is 36.
    • There's also the Ship Tease between Heileen and Elias, who Heileen notes is handsome, though he's much older than her.
  • Mistaken for Cheating
    • In one of the flashbacks, Heileen mistakenly thinks that Lora is cheating on Otto with Jonathan, when she overhears Jonathan remarking how beautiful Lora is. She then finds out that Jonathan was only painting Lora's portrait, which Lora was planning to surprise Heileen with, as a gift.
    • One night, John and Heileen are following Ebele around because they suspect her of cheating on Robert with Jonathan. Ebele goes into Jonathan's room for awhile, and when she emerges, she finds John and Heileen hiding behind some supplies. When they announce their suspicions, both Jonathan and Ebele laugh and find it amusing that Heileen and John would think they were together. Jonathan was only tutoring Ebele in Latin.
    • John's ending. Heileen finds Lora sneaking off to meet him in a cabin. Turns out it was a set up by John and Lora to get Heileen to confess her feelings for him.
  • Multiple Endings: All three games have multiple endings based on what characters Heileen romances. The third game also has multiple career-based endings that Heileen can obtain based on her skills and moral alignment.
  • Not What It Looks Like
    • Marco's horrified when he finds Marie on her knees in front of Jack. Unbeknownst to Marco, Marie is only (platonically!) thanking Jack for saving her life. Heileen finds this hilarious and lampshades the fact that it essentially looks like she's giving him oral sex.
    • When Heileen tries to explain to Lora, Marie and Ebele why she's chasing John around the bridge, she shows them her bound wrists. They mistake this for a bondage thing.
      Lora: Oh my, I had no idea you kids were into that!
    • In another instance, Heileen assumes that Morgan and Juliet must have had a wild night when she's asked to help Juliet clean up Morgan's trashed room. They were just arguing, and Juliet has the tendency to throw things around when she's angry.
    • And in another scene, she overhears Lora massaging Marie in her room after she injured her back, and mistakes Marie's moans for something more sexual.
  • Protagonist-Centered Morality: Heileen can choose to have relationships with as many people as she prefers, and the system won't judge her for this. This is especially egregious in the third game when she tries to expose Ebele for allegedly cheating on Robert, and is particularly hypocritical if you're also pursuing Ebele as a love interest at the same time.
  • Scoring Points: In the first and second games you need to solve quests, and the accumulated points determine which ending rank you receive.
  • Tarot Motifs: Heileen finds 14 tarot cards representing the Seven Heavenly Virtues and Seven Deadly Sins in the second game, which have the ability to alter reality. This format branches off into the third game, where your morality alignment determines which professions Heileen ends up with.
  • Tone Shift: The first game is more dramatic (dealing with suicide, near-rape, and freeing slaves), the second game is more reminiscent and contemplative (dealing with memories, choices, and reality within dreams), and the third is more adventurous and slides into romantic-comedy territory (introduces slapstick and farce, centers on romances and pirates).

    Heileen 1: Sail Away 
  • Attempted Rape: Burt tries to rape Heileen in Lora's ending when they're on the lifeboat and he's convinced that they're all going to die. Lora attacks and kills him with a knife to defend Heileen.
  • Early-Installment Weirdness: Heileen can't understand Black, but in later games, he speaks directly to her.
  • First Kiss: Canonically, Heileen receives her first kiss from John. Instead, she can receive her first kiss from Marie.
  • Footsie Under the Table: Under the dinner table, Marie massages Heileen's feet, which embarrasses Heileen and causes her to slide out of her chair and fall onto the floor.
  • Got Volunteered: Jack is only travelling to the New World because he is an indentured servant.
  • Guys are Slobs: During arm-wrestling matches between the sailors on the Cat's Dream, Heileen notices the men yelling, drinking and spitting on the ground. Whether she finds this disgusting or enthralling is up to the player.
  • Heroic BSoD: Heileen has one at the end of the game when she realizes that Marie sacrificed herself so that Heileen could get off the ship. Heileen deludes herself into thinking that it's All Just a Dream.
  • Heroic Sacrifice: Marie plays this straight when she shoves Heileen into the lifeboat, with no space left for herself. Subverted when Heileen tries this in Marie's ending, but Marie pulls her down into the lifeboat with her.
  • In Vino Veritas: Marie confesses that she loves Heileen after drinking too much wine at the party.
  • Mood Whiplash: One minute, Heileen and Marie are enjoying themselves at a party; the next night, Marie tries to commit suicide.
  • Near-Rape Experience: Elias gropes Heileen when they're alone together. When she rejects him, he continues trying to seduce her and almost assaults her. Jack ends up stopping Elias, and Elias becomes shocked that he even tried to have sex with Heileen in the first place.
  • Nightmare Sequence: The night of the storm, Heileen has a nightmare where she feels something sticky and realizes that her fingers are bleeding... then her nose and her mouth start bleeding, and she realizes that she's bleeding everywhere.
  • Out-of-Character Moment: In an early version of the first game, Marie only shows signs of romantic affection for Heileen—she even gives her her first kiss. But after some Mood Whiplash when Marie attempts suicide, she confesses that she's in love with Marco and only tried to slit her wrists so that he'd pay attention to her. Heileen accepts that Marie loves Marco without question, but before this point Marco and Marie had barely exchanged words and there were no signs that there were sparks between them. Thankfully, this is corrected in a later version of the game, where Marie only attempted suicide out of loneliness and wanting to be with Heileen.
  • Ship Tease: Between Heileen and Elias, who Heileen is initially attracted to, although the Ship Sinking happens soon after.
  • Slave Liberation: Lora and Otto bought Ebele and Robert as children in America in order to free them from being bought by a plantation owner. They then brought them back to England and pretended that they were their own slaves, meanwhile raising them to adulthood.
  • Take My Hand!: After Heileen's handkerchief flies away, Marie practically dives overboard to grab it. This leads to Heileen trying to lift Marie up, rather unsuccessfully, until Jack comes by and helps them.
  • The Unfair Sex: The tone throughout the first installment. Heileen and Marie constantly remark how all men are pigs, and Heileen assumes that John only wants to see her naked.

    Heileen: A Trip to Bavaria 
  • At the Crossroads: Bavaria serves as a sort of crossroads for Heileen about her feelings towards the New World. She can choose to be reluctant about travelling with Lora and Otto, or she can choose to willingly leave the Old World behind. Regardless, the plot requires that Heileen leaves.
  • Bittersweet Ending: In all endings, Heileen leaves Magdalene even though they have feelings for each other.
  • Foregone Conclusion: Due to this game being a prequel to Heileen 1: Sail Away, the ending is inevitable: Heileen leaves Bavaria because she travels to the New World.
  • Please, Don't Leave Me: Magdalene confesses that she wants Heileen to stay just as she's about to depart with her aunt and uncle.
  • Uptown Girl: Heileen's and Magdalene's friendship hints at this sort of relationship. Magdalene is the poor farmgirl who's fallen for Heileen, the rich noble.

     Heileen 2: The Hands of Fate 
  • Arranged Marriage: Lora reveals that she was set to marry the Duke of Manchester, but refused because she wasn't in love with him.
  • Artifact of Doom: The knife from Heileen's dream possesses Robert/Ebele and causes one of them to attack her. Luckily, the Heileen manages to get them to drop the knife before she gets hurt.
  • Ax-Crazy: Heileen's dream with Jack ends with him supposedly swinging an axe down on her head.
  • Because You Were Nice to Me: One of the reasons Morgan allows Heileen and her friends to stay on the ship is because she didn't rat him out when he stole her wallet, and allowed him to keep the money.
  • Cassandra Truth: Briefly, when Heileen warns the pirates that the island's natives are planning an ambush. They don't believe her, until they're being shot at with arrows a few minutes later.
  • Chekhov's Army: The group of natives that Heileen encounters earlier in the game later ambush Morgan's crew onshore.
  • Chekhov's Gunman: Marcus/Morgan appears earlier in the game as one of Heileen's classmates. He then shows up again at the end of the game as the pirate who rescues her from the island.
  • Cutting Off the Branches: The first game has three endings for John, Marie and Lora. None of these is the canonical ending, as the second game instead has Heileen, Ebele and Robert stranded on an island.
  • Christianity is Catholic: The school that Heileen, Marie, and Marcus went to as children was Catholic.
  • Corporal Punishment: Sister Anna intends to beat Marie when she finds her playing in the chapel.
  • Dreaming of Things to Come: Heileen has a dream where the young Marcus shifts into his older self... but is confused by his eyepatch, which makes him look like a pirate. He shows up at the end of the game, where he actually is a pirate that helps Heileen and her friends off the island.
  • Dreaming the Truth: From the documents she finds washed ashore and the memories in her dreams, Heileen deduces that her parents abandoned her in the woods when she was young. Jack found her and took her in as his child. Her parents have second thoughts and come back to claim her, but are later killed in a bridge accident.
  • Early-Bird Cameo: Jonathan shows up, although Lora refers to him as John. Heileen mistakes their encounter as Lora cheating on Otto while he's away. Later, it's revealed that Jonathan was only at their home so he could paint Lora's portrait.
  • Fetch Quest: This is incorporated into the story: Heileen must make the right choice in her dreams in order to obtain items for either Robert or Ebele, so that they can get off the island.
  • Flashback: Heileen's dreams are all events from her childhood or pre-teen years, so it's as if she's reliving memories.
  • Hostage Situation: Subverted. Robert pretends that Heileen is his and Ebele's hostage when the pirates land ashore in order to protect her.
  • Law of Inverse Fertility: Although Lora wants to have children, the doctor mentions that she's infertile. This is why she considers Heileen her daughter.
  • Like a Daughter to Me: Lora says that Heileen is like a daughter to her, and that she would be proud of her if she won the beauty contest. The fact that Lora can't have children also contributes to her warm feelings towards Heileen.
  • Luke, I Am Your Father: Captain Adam reveals that he's Otto's father to Heileen. Otto doesn't realize they're related because Captain Adam never saw his children.
  • Maybe Magic, Maybe Mundane: The tarot cards and the island. Heileen first believes that her dreams are just memories, but when items consistently appear after she wakes up, she begins to think that something magical is at play. Ebele realizes this as well, and considers the island to be magical.
  • Memento MacGuffin: Juliet's sword, engraved with "For my beloved Juliet,'' was a gift from her father.
  • Mirror-Cracking Ugly: Ebele jokes that Robert's reflection would make the hand mirror crack.
  • "Not Wearing Pants" Dream: One of Heileen's dreams has her competing in a beauty contest in front of hundreds of people in only her underwear.
  • Or Was It a Dream?: Heileen wakes up to find one of the biscuits from her memory/dream right in her pocket. This later happens with other objects she needs.
  • Quicksand Sucks: Heileen gets stuck in some quicksand and starts sinking quickly, until Robert rescues her.
  • Please Put Some Clothes On: Juliet gives Heileen an extra outfit, since her torn and Fanservicey dress is attracting the attention of the pirates.
  • The Reveal: Jack didn't kidnap Heileen—Heileen's parents abandoned her in the woods with Jack.
  • Robinsonade: The entire game takes place on the desert island that Heileen is shipwrecked on.
  • Rope Bridge: Heileen, Ebele, and Robert have to cross one in order to get to the opposite side of the island they're shipwrecked on. The bridge crumbles as Heileen runs across, but she has a rope that the others can use to cross the river.
  • Suck Out the Poison: Heileen tries this when Robert gets bitten by a venomous snake. In true Hollywood fashion, it works, although Ebele had the more reasonable idea to mix herbs in order to create a sort of anti-venom.
  • Sliding Scale of Idealism vs. Cynicism: Central to the plot and embodied through the dreams and tarot cards. If Heileen is idealistic, she'll make it to the end of the game and sail off the island. If she leans towards cynical, she'll toss the tarot cards into the fire, and accept that they're stuck on the island, but with the small hope of moving on with her life after her friends' deaths.
  • Third-Option Adaptation: All of the endings from Heileen 1 are All Just a Dream, and Heileen ends up on the island with Ebele and Robert.
  • Total Eclipse of the Plot: Heileen bluffs the natives into releasing her and her friends by conveniently using an eclipse to pretend she has magical powers.
  • Trademark Favorite Food: It's revealed that Heileen's favorite breakfast food is milk and biscuits, since she asks for this every morning.
  • Vision Quest: The second game is structured as a sort of quest through Heileen's dreams. Heileen relives moments from her childhood and near past in order to gain closure after her friends' (assumed) deaths on the shipwreck. In her dreams, she sees all of her friends and family, and the experiences teach her something about her own personality. There's also the Maybe Magic, Maybe Mundane element at play as to whether her actions in the dream can alter reality or whether they're just fantasy.
  • What the Hell, Hero?: Black sometimes calls out Heileen for her selfishness and misdeeds when she favors the sins.
  • You ALL Share My Story: In her dreams, Heileen realizes that everyone who was on the Cat's Dream was connected somehow, either as relatives, or they met sometime in the past.
  • You No Take Candle: This is how Robert and Ebele speak. Surprisingly, this is dropped in the third game: when Robert slips up early on, Ebele immediately corrects his grammar and Heileen remarks on how much their English has improved.
  • Your Mind Makes It Real: Heileen can feel pain in her dreams.

    Heileen 3: New Horizons 
  • Accidental Kiss: Lora tries to kiss Heileen on the cheek as a thank you, but ends up tripping and kissing her on the lips.
  • Affectionate Gesture to the Head: Lora strokes Heileen's hair when trying to convince her that they should stay onboard the ship instead of continuing their journey to the New World. Other characters also frequently pat Heileen's head affectionately, namely Morgan, Sebastian, and Jonathan.
  • Almost Kiss: Happens a few times on the ship between Heileen and her love interests. Usually interrupted by one of the other characters walking into the room in a Moment Killing sequence.
  • Awesome Anachronistic Apparel: Inverted: If Heileen chooses to do the Navigator activity, her Super-Deformed self is shown wearing a cowboy hat and denim short shorts.
  • Bar Brawl: Juliet instigates one when Morgan breaks off their relationship to be with Heileen.
  • Bear Hug: Sebastian's method of winning duels with Heileen. Instead of facing off directly against her, he just charges her and lifts her into the air in a bear hug.
  • Beautiful Dreamer: Happens between Heileen and her love interests. Usually, it's Heileen watching the other characters sleep, but John once observes Heileen sleeping in her room after taking refuge from the storm there.
  • Better as Friends
    • Morgan and Juliet. They dated before, and Morgan even proposed to Juliet, but they broke it off when Juliet realized she couldn't return Morgan's feelings.
    • Ebele and Robert as well in Ebele's ending. They mutually decide that they no longer love each other and break up.
  • Big Damn Heroes: Juliet pulls one of these when she rescues Heileen from the pirate gang that attacks her.
  • Call-Back: To the diamond that Otto is looking for, in Sebastian's ending. Sebastian does find the diamond, and he and Heileen live Happily Ever After.
  • Cannot Spit It Out: Jonathan's ending. Heileen has a few Once More, with Clarity moments where she sees how Emotionally Tongue-Tied Jonathan has been around her.
  • Cock Fight: John and Sebastian almost physically fight over a disagreement involving Heileen.
  • Crush Blush: Heileen blushes when she tells Morgan she had her first kiss with John. Though she's embarrassed, he remarks that it's cute.
  • Crushing Handshake: When Morgan first meets John, he delivers a strong handshake that makes John wince in pain.
  • Distracted by the Sexy: When Lora comes aboard the ship, some of the pirates start having accidents because they were staring at her instead of focusing on their work.
  • Eating the Eye Candy: Heileen can't help but notice that Sebastian is half-naked and muscular when he first walks into the room. She has the same reaction when she's distracted by Morgan's chest.
  • Erotic Eating: In both Marie's and Ebele's paths. In the former, Heileen licks cake off Marie's finger, and in the latter, Ebele feeds her fruits.
  • The Drunken Sailor: Morgan, his crew, and Heileen and friends can be found drinking throughout the third game, whether it's wine or rum. Morgan jokes that they're not drunk all the time, just most of the time.
  • Family Friendly Strip Club: The Red Lantern. The dancers are scantily dressed, but not topless.
  • Groin Attack: Juliet threatens Marco with one if he hits her in the head with his frying pan again.
  • Hard-Drinking Party Girl: Sebastian mentions that this is his type.
  • Hilarity Ensues: Physical comedy usually courtesy of Marco, although Heileen gets in on this as well.
  • How Much Did You Hear?: Combined with a Love Confession in Sebastian's ending. Heileen thinks Sebastian has made a life-risking dive to obtain a large diamond. She confesses her feelings in the open when she believes he's dead. He then walks out from behind her and reveals he hadn't yet gotten in the water.
  • I Kiss Your Hand: Heileen gets jealous when Morgan kisses Marie's hand to welcome her to the ship. Sebastian also kisses Heileen's hand and thanks her for convincing Morgan to allow Sebastian onboard the ship.
  • Like an Old Married Couple: Morgan and Juliet are constantly bickering or arguing, but out of concern for each other. Heileen lampshades this and remarks that she and John are the same way.
  • MacGuffin: The diamond that the Morning Star's crew is searching for, though this objective takes a backseat to the relationships.
  • Making Love in All the Wrong Places: Sebastian's ending. Heileen loses her virginity to him on the beach.
  • Male Gaze: The camera focuses mostly on Lora's assets during her dance at the Red Lantern. Heileen is also subjected to this during her dance on the ship.
  • Manly Tears: Otto starts crying when it's clear that he misses Lora.
  • Memento MacGuffin: Jack carves a horse figurine for Heileen, as a symbol of their parent-child relationship when her parents abandoned her in the woods.
  • Moment Killer: Happens in a few encounters between Heileen and her love interests. Heileen and John are about to kiss, when Lora checks in on them. In another instance, Heileen and Morgan are about to kiss when Juliet calls out to Morgan.
  • Naughty Under the Table: In Ebele's ending, combined with Erotic Eating during a candlelight dinner.
  • No Guy Wants to Be Chased: Gender flipped with Juliet and Jonathan. Jonathan constantly chases after Juliet to ask for her permission to paint her. She only relents when he grabs her wrist and refuses to take no for an answer.
  • Operation: Jealousy
    • Jonathan tries one of these by having Heileen model for him in order to make Juliet jealous. This backfires a bit, when he's struck by Heileen's beauty.
    • In his ending, John confesses that he flirts with other girls in order to make Heileen jealous. It works though she doesn't admit it.
  • Over-the-Shoulder Carry: Sebastian lifts Heileen up and carries her like this when he loses to her in their practice duel.
  • Pirate Girl: Juliet, and Heileen and Lora once they join Morgan's crew. Some of Heileen's dialogue choices have her bragging about being one. Becoming a Pirate is one of the occupational options as well.
  • The Pirates Who Don't Do Anything: At first, Morgan and his crew don't seem to be involved in any skirmishes, but this is justified when Juliet explains that Morgan deliberately avoids getting into fights in order to protect Heileen and her friends. This is subverted when they later end up in a battle with another ship.
  • Previously on…: The third installment starts by recapping the main events of Heileen 1 and 2, both to quickly catch up new players and to remind returning players of the main plot.
  • Punch Catch: Jonathan catches Heileen's fist during their playful mock fight.
  • Raising Sim: The third game shifts into this format, which include a couple of stats screen and skill-building. However, the relationships you pursue don't rely on your skill set, unlike in a Dating Sim—Heileen's success in pursuing others depends solely on the choices she makes in conversation. The skill sets only affect the ending if you don't end up with a love interest—instead you end up with the corresponding profession whose skill and virtue/sin you've maxed out.
  • Running Gag: Juliet threatening to throw anyone who annoys her to the sharks.
  • Secret Character: Discussed in a comedic outtake, where Heileen tries to use the Konami Code to cheat and see if Black is a hidden love interest.
  • Secret Diary: Heileen, Marie and Ebele stumble across a diary that John drops, and consider reading it to see if John has written about any of the girls. John sneaks out from behind them, and remarks that it's not his diary, but Jonathan's, since Jonathan asked John to bring his things to the workshop.
  • Shameful Strip: Happens to Marie when she rashly decides to wager her clothes in a dice game against Sebastian. Sebastian cheats, of course, and Marie ends up having to strip down to her underwear in front of a group of pirates if Heileen doesn't chase off Sebastian.
  • Shout-Out
    • To Donkey Kong, of all things. Heileen and Marie make fun of Juliet and compare her to an ape that throws barrels.
    • In an outtake, Morgan explicitly mentions Shark Week.
  • Slap-Slap-Kiss: Morgan's ending. Heileen's angry at Morgan because she thinks he's dumping her for Juliet, and has a flintcock pistol pointed at him. He wrestles the pistol from her and they kiss.
  • Spit Take: At an island restaurant, Morgan, Heileen and Juliet ask to see the cook to thank him for the food. Heileen spits her wine all over Juliet when she sees that that cook is Marco.
  • Standard Female Grab Area: Despite her strength, Juliet finds it painful when Jonathan grabs her wrist, and only then agrees to allow him to paint her portrait.
  • Talk Like a Pirate: Lampshaded in one of the comedic outtakes. Morgan makes an effort for all pirates to speak eloquently in order to break this stereotype. All the pirates agree with him and respond, “Aye! Aye!''
  • Tears of Joy: Shed when Heileen and Marie finally reunite after they've found everyone else. Ebele also sheds these after she reads Heileen's preface to her book.
  • That Came Out Wrong: An extended encounter between Heileen, Marie and Sebastian has Heileen in the following innuendo-laden conversation. She's completely unaware of the sexual implications until Marie points them out to her, after which she turns beet red and clarifies that that's not what she meant.
    Heileen: I just wanted to sleep with him, that's all.
    Marie: You're just gonna go ahead and sleep with him, out here in the open?!
    Heileen: Well, we're only gonna do it for a few minutes, so I don't see the point of going anywhere else. Besides, it'll be comfortable here. You should join us, you know.
    Marie: Me?! Join you?! No way! I never thought I'd see the day that you'd ask me to join you in a threesome!
  • There Is Only One Bed: When Ebele spends the night in Heileen's cabin, which predictably leads to Sleep Cute.
  • Toilet Humor: In a comedic outtake, Lora eats a bean casserole before performing her dance, leading to Fartillery that not only clears the room, but sinks the entire ship. Another one has Otto driving off attacking pirates by burping.
  • Watching the Sunset: Heileen and John watch the sunset together over a bottle of wine. This also happens with Heileen's other love interests, such as Marie and Ebele.
  • What Happened to the Mouse?: While Otto mentions that Captain Adam died, no one asks what happened to Burt, most likely because he was an unsympathetic Jerkass. It's possible that he was Killed Off for Real, as seen in Lora's ending in Heileen 1.
  • Who's on First?: The following exchange happens when Heileen and John are practicing knot-tying, and Heileen allows John to practice tying a hitch knot around her wrists.
    Heileen: Can you release me?
    John: I will not.
    Heileen: I don't want you to knot, I want you to unknot!
  • Wooden Ships and Iron Men: Morgan's crew ends up in skirmishes with other ships, and trade and steal goods to maintain their life at sea. Although Morgan's crew seems particularly non-violent at first, this is played straight when Heileen witnesses the bloody and destructive aftermath after a battle. To note, though, not all of Morgan's crew consists of men.
  • You're Insane!: Morgan's reaction to Jonathan's suggestion that he pay in order to travel with pirates.

Alternative Title(s): Heileen 2 The Hands Of Fate, Heileen 3 New Horizons