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.
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.
Heileen starts her journey as a spoiled and sheltered rich girl who is sexually innocent and naïve about others less fortunate than her. Across all three games, she (ideally) develops into a more caring and giving person, learns useful skills, and falls in love.
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.
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.
Played straight when Marie tries to commit suicide by cutting her wrists—Lora stops her in time.
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.
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.
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.
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.
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.
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 vices and virtues in the second game. The tarot cards 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.
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 starts 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 aboard 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.
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.
Lie Back and Think of England: Heileen's attitude when she carelessly loses her virginity to Jonathan in one of her dreams, before they're married.
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.
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 catds. 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.
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—it ends up seeming like Ebele and Robert learned perfect English overnight.
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.
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.
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.
Groin Attack: Juliet threatens Marco with one if he hits her in the head with his frying pan again.
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.
Male Gaze: The camera focuses mostly on Lora'sassets 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.
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.
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.
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.
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.
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.
Your Cheating Heart: Heileen catches Lora making out with Sebastian in his cabin. She stops him when she hears Heileen crying, and is completely apologetic about cheating in the first place.
You're Insane!: Morgan's reaction to Jonathan's suggestion that he pay in order to travel with pirates.