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  • Awesome Ego: Jenny is spectacularly vain, believing that she should just get whatever she wants because she's the hottest girl in the world. Reading her diary is quite hilarious for how absurdly solipsistic it is.
  • Complete Monster: Dimitri stands out as a remarkably dark villain in an otherwise lighthearted Dating Sim. An enforcer for The Mafiya and the right-hand man of Raznikov Putin Chernyshevsky, who have recently moved into Summerville to build a criminal empire with drugs and Human Trafficking, Dimitri murdered Frank Cummings before harassing and extorting the Main Character's family to retrieve the money Frank owed them. Dimitri eventually tries to kill a cop and kidnaps the Main Character's stepmother and stepsister when he proves to be a thorn in their side, preparing to rape and murder both of them before attempting to kill the Main Character while gloating about his father's murder.
  • Ensemble Dark Horse:
    • Eve for her tragic backstory and believable storyline.
    • Jenny for being hilariously arrogant and egotistical.
    • Miss Dewitt is the most popular of the teachers with fans, both for her Ms. Fanservice qualities and having the nicest personality. There is more Rule 34 of her than there is of the other teachers.
  • Escapist Character: The Main Character is one for horny teenage boys. Despite being relatively plain in all other respects, he's hung like a moose, has sex with nearly every woman in townnote , gets the Alpha Bitch to dump her boyfriend for him, beats said Jerk Jock boyfriend into a pulp after humiliating him, and gets to hang out with Mario, John Wick, and Ivanka Trump before almost single-handedly disposing of The Mafiya, avenging his father's death, and ending up with a Cool Car, a beach house and a loaded bank account, and possibly becoming a father several times over (without the burdens of things like child support or having to invest any time in raising the babies).
  • Fan-Preferred Couple: Judging by the amount of fan-art, players seem to love the idea of pairing up trans Eve with Kevin, despite the obvious issues. They both help out the MC with the music contest but otherwise display no interest in each other, with Eve as a possible partner for MC himself, while Kevin is hinted to have a hidden crush on him.
  • Funny Moments:
    • After Kim is forced to flee the country, his wife defaces his statue by giving him an apron, lipstick, and putting a dildo on his head.
    • To prevent Mrs. Smith and Annie from disturbing the High School Talent show, the MC and Erik break into the school the night before to apply a very strong glue to their chairs in Mrs. Smith's office. And sure enough, they both get stuck on them. When they eventually do show up at the Talent show near its end, Mrs. Smith's skirt has several cracks and a red seat cushion is still glued to Annie's
  • Growing the Beard: For its first few years of development, the game was a pretty simple open world dating sim where you could interact with the girls for a bit, occasionally having to engage in a couple of fetch quests or minigames, until you got to have sex with them. Roxxy's story update marked a significant upgrade over previous routes, completely reworking the previously one-dimensional Hate Sink Alpha Bitch by revealing considerable Hidden Depths that took her from one of the least-popular girls (character-wise at least) to one of the most-popular. Eve's route raised the bar even higher, giving her a startling deep and convoluted story based around her complicated relationship with her sister Grace and her crippling self-esteem issues, as well as including the option for her to be a transgender girl, and also featuring several teases towards the game's more-serious central storyline.
  • Guide Dang It!: The cave maze in Aqua's route. Are the fish a hint on where to go? No. What about the arrows you press in the octopus fight right before it? No. The solution is the world map in the MC's attic, with no obvious link to the caves. Furthermore, it's extremely likely that you would have discovered the map long before encountering Aqua and make the assumption that it had something to do with the mafia storyline than anything else.
  • Harsher in Hindsight: While Russian President Vladimir Putin already had a reputation for silencing political opponents through assassination, his portrayal here as a ruthless and humorless leader of The Mafiya is possibly harder to watch after the 2022 Russian invasion of Ukraine and the thousands of deaths that resulted from it.
  • Heartwarming Moments:
    • In a later update to the main story, when the MC hands Jenny a photo of her as a child with Frank, she hugs him and genuinely thanks him. As far as we've seen, this is the sweetest that she has ever been to anyone.
    • Tony discovers that he is infertile after he and his wife Maria have been trying to conceive for a while. He then asks MC to be a sperm donor, setting up the impregnation in the backroom of their pizzeria, and can even cheer him on during the act.
    • The entirety of Eve's storyline. She starts out as a lonely girl with self-esteem issues who's seemingly disliked by most everyone in the school. But after becoming close to the MC, she comes out of her shell and breaks free of her insecurities. And the dialogue between them is just... awwww.
  • Incest Yay Shipping: Too much to count. While all incest storylines, of which there are many, were (officially) removed from the game in later updates, players continue to ship them. This even extends to characters who've never shown any canon interest in each other, such as Mia and her dad.
  • Memetic Loser: Even moreso than in the game, Dexter is a comically pathetic loser in fan-art, such as crying like a bitch after Roxxy sends him texts that MC is cuckolding him; or being the bottom to Eve, who then shares this knowledge with the entire school.
  • Nightmare Fuel: Not a whole lot, but every now and then, a genuinely tense and/or terrifying moment can find its way into this otherwise lighthearted game.
    • The MC going to Principal Smith's house to steal Roxxy's graded tests. The hallway to her bedroom — and the bedroom itself — is decorated by satanic and otherwise sinister imagery, and there's a creepy hole in the basement sealed off by a grate. Just as he grabs the exams, Principal Smith walks in and with seconds to spare, he slips out the window. Makes you wonder, coupled with the creepy hooded figures you see in the school on an unrelated quest just what she's really up to, on top of being an insufferable tyrant.
    • Everything about Dimitri. He's a genuinely menacing and absolutely reprehensible character. While most of the Hate Sink or otherwise antagonistic characters at least have some humorous qualities, he doesn't, apart from a few interactions with his dimwitted henchman Igor. One of his first interactions with the MC is to threaten to rape Debbie, which he very nearly makes good on late in the main storyline, alongside torturing her and Jenny. Dialogue with one of the prostitutes also implies that he has tortured and killed dozens of them.
  • No Yay: Dimitri is sometimes shipped with other characters for purposes of Vulgar Humor. After all, in-canon he is a sex trafficker and a rapist.
  • Scrappy Mechanic:
    • The Pizza Delivery minigame. From a certain point, progression in the main plot is gated behind playing this single simplistic and rather dull minigame over and over again, whether you need the money or not, and it's further gated when you're repeatedly forced to spend money to buy a better vehicle to do deliveries better, which only makes the game harder but no more interesting. To add insult to injury, even if you're playing in cheat mode, it's the only minigame you cannot skip.
    • Speaking of which, the whole reason the game has a cheat mode (which starts you off with maxed stats and money and allows you to skip almost all the minigames) was to compensate for a different problem, namely that for the first couple of dozen versions of the game saves were not compatible with each new release, forcing players to start over from the beginning every time a new update came out. Cheat mode was meant to cut down on the amount of repetitive grind you'd have to do to get back up to where you were. Fortunately DarkCookie eventually worked out how to get save compatability to more-or-less work.
  • The Woobie: Eve is probably the most distraught and withdrawn character in the story, and befriending and starting a relationship with her turns her into a much happier character.

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