Death Match Love Comedy is a simple concept. If you fall in love, you will explode. If someone confesses love to you, you will explode. You also are going to school, meaning if your school day romance goes south, you will, in fact, violently blow up at a school. Obviously, you playing any game that suggests volatile detonation in a school setting will probably concern your government.

You ever look at your computer equipment and feel a strange sense of attraction? Apparently, whoever plays the absurd dating sim Brother Falls in Love! might be feeling some tension between themselves and their printer. The game is a schoolboy romance featuring a romantic relationship between the main character and a sentient, soccer-playing printer. I know some people are enthusiastic about computers, but...this is ridiculous.

School Days is an almost easy answer to the question “What is the most twisted dating sim you can find?” The game received a fairly infamous reputation early on due to its secret murder endings – endings that would later be used as inspiration for its anime adaptation. However, where School Days really excels is just how creepy the whole experience feels. It feels sleazy, knowing that you’re courting and playing with the hearts of girls this profoundly unstable. It feels...crueler than other dating sims for that reason.

Creature To Koi Shiyo! Kokonoe Kokoro asks the intense questions every degenerate asks themselves: if you had a chance to date an insect, would you? Obviously, this absurd concept is a little out there, but that’s what happens when you boot up this dating sim. A cricket-girl in a school-girl uniform flirts with you. That’s...got to amount for something.

Divi-Dead is an old school eroge visual novel, first being released back in 1998. You play a sickly boy hired by his uncle to spy on a school. What you find is, in short, a pure descent into madness and human depravity. This is a distinctly adult game, showcasing some truly horrific material throughout that can only be tangibly regarded as a dating sim. Still, playing this game leaves you suspecting that someone is going to come knocking on your door asking for your internet search history.

Uma No Prince-Sama feels like it should be breaking some laws. In this very simple dating sim, you are a girl dating a handsome boy. This isn’t so strange on the surface, but it gets weirder when you consider that the love interest is a horse with a human head. You basically feed the horse carrots, get them to run and train, but – why a horse? Why would someone want to date a horse? This mobile game feels like something….wrong.

Osananajimi Wa Daitouryou: My Girlfriend is the President offers a relatively wholesome concept. Your next door neighbor, a young girl, is turned into the president by aliens. Everyone is brainwashed into accepting this – save for you, the protagonist. Now, due to your pre-established relationship, you embark on your goal: get with the uncomfortably underage president. Oh, and one of the president’s cabinet members is a sentient UFO who takes the form of a pretty girl. Also, sexy Vladimir Putin. This game is something.

Gore Screaming Show – well, let’s be honest. You know what you’re getting into with a title like that, don’t you? This one centers on a school boy looking for ladies, only to uncover an enigmatic cult that sacrifices women brutally, violating their bodies in unspeakable ways. Worse still, the cult might be tied to his own family. Gore Screaming Show is a showcase of brutal artwork and disturbing concepts. There are no moments in this game where something brutal isn’t transpiring before your eyes.

Song of Saya is not necessarily a dating sim, but the core concept involves you dating what can only be described as an otherworldly entity of nightmarish reality. After an accident, the main character of Song of Saya is left with a debilitating condition: everything is gory and grotesque. Save for one girl named Saya...who inspires unimaginable terror in everyone else who sees her. Things only go worse from there.

RapeLay really stretches what “counts” as a dating sim. The game centers on a man who stalks and assaults a family, systematically tracking them down to assault them. This game is infamous for being banned in numerous countries. In reality, this game IS going to get you on a watch list, depending on what country you play it in, because the game is still very much illegal. Play at your own risk.