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The end result is gaming concepts so ludicrously brilliant and strange that sometimes Steam users purchase them just to answer the question, “How could this game possibly work?” throughout. While a few of the following games are completely interchangeable with other titles in their respective categories, their core concepts are quite attention-grabbing.
Updated March 1, 2021, by Thomas Bowen: There’s a very fine line between funny and weird and which side of that line a game falls on can often vary from player to player. Some games, however, are so far out there that it’s difficult to muster a chuckle due to their bizarre and, at times, insane premises. As the popularity of dating sim games has risen, so too has the number of these weird and wacky titles finding their way onto Steam. For fans of the peculiar, there has never been a more ‘interesting’ selection of dating sims to choose from.
15 Hilarious: PacaPlus
PacaPlus sets out to answer that age old question that has eluded mankind since the dawn of time: What would happen if one’s partner suddenly turned into a talking alpaca? Admittedly, it’s probably not something that too many people have wasted their time thinking about, but anybody intrigued by the concept can certainly find out here.
The game’s creators are clearly aware of how bizarre the premise is and lean into it at every opportunity they get. By embracing this goofiness, they’re able to keep the tone of the game light and this in turn leads to plenty of hilarious moments. It’s surprisingly well written too and the voice acting is solid throughout.
14 Weird: Furry Shakespeare: To Date Or Not To Date Cat Girls?
One probably has to be amongst the target audience to really ‘get’ what the developers of Furry Shakespeare: To Date Or Not To Date Cat Girls? were going for here, but it will likely be lost on the average gamer. The problem is though, it’s not immediately obvious who exactly this game was designed for. That, and there aren’t nearly enough cats.
Its feeble attempts at humor are crass and unfunny and there’s not really any kind of coherent narrative to speak of. The idea of dating Shakespearean characters itself is actually quite an interesting one, but its implementation is such that it just feels strange.
13 Hilarious: Panzermadels: Tank Dating Simulator
For anybody who has ever wondered what it would be like to date a tank, then Panzermadels: Tank Dating Simulator is probably a pretty good point of reference. It’s funny too; at least for those with a high tolerance for innuendo and the kind of jokes that only the dadliest dad would ever dare tell. This is only a small part of the game though.
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Beneath the surface, there’s actually some wonderfully creative historical humor that really fits in well with the tone and theme of the game. The personification of the tanks as waifu style women is an interesting idea too and, provided it’s not taken too seriously, makes for an enjoyable and funny experience.
12 Weird: Death Match Love Comedy
What is funny and what is weird can vary dramatically from region to region. While there’s certainly some common ground, eastern humor can sometimes be a little jarring to those in the west. That is definitely the case with Death Match Love Comedy.
The ‘Comedy’ that’s referred to in the game’s title is typically centered around death scenes and bizarre interactions with classmates. Due to the lack of voice acting and there being no English language translation though, only those who can read Japanese kanji will be able to find out just how weird it truly is.
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10 Hilarious: Flirt
From the creators of Comedy Night, Flirt is a game that pairs random strangers into a chat room with custom avatars and asks them to simply flirt away. When someone has a positive interaction, they can leave the other person some love and raise their heart level, showing others searching that they are super smooth.
While this doesn’t fit exactly with the other entries on this list in terms of gameplay, one can’t get much closer to simulated dating than Flirt. With a dating sim like this, who needs Tinder, right?
9 Weird: Angels With Scaly Wings
If one has ever wondered what it would be like to date a dragon, then Angels With Scaly Wings is perfect for them. The player stumbles across a world populated by dragons and journeys to meet the citizens of the town, falling in love every step of the way.
Angels With Scaly Wings has 13 different endings that vary depending on a player’s experiences having coffee, consoling, or solving murder mysteries with dragons. The strangest part is this concept could have worked well with human characters, so one must wonder why the developer decided to go with dragons. There is truly a game for everyone out there.
8 Hilarious: Purrfect Date
After being transported to Cat Island for research, the player starts to realize something seems fishy. The only logical way to get to the bottom of the mystery is, clearly, to date cats.
In Purrfect Date, the player decides to romance friendly felines in the hopes of uncovering the secrets behind Professor Pawpur. The game has 18 different endings with many branching story paths, dialogue options for each conversation, kitty dates, and more cat puns than anyone could ever want or need to hear in their lifetime. In other words, it’s a great dating sim.
7 Weird: Dream Daddy
The idea is simple. As a dad, you are on the prowl searching for other dreamy dads to fall in love with. Actually, no, that isn’t that simple. The issue with Dream Daddy that makes it weird isn’t necessarily the concept, rather it’s the way that the game goes about it.
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This game includes seven different dateable fathers, each with multiple endings. There are also many minigames and such to play during each date, along with so many dad puns that nobody will forget for a second just exactly what they are trying to accomplish in this game. The romance and minigames in Dream Daddy can be strange, and that’s okay. Sometimes players just need to date some dads.
6 Hilarious: Speed Dating For Ghosts
Speed Dating for Ghosts is a game where players get the chance to talk with over a dozen ghosts from different periods and learn about their life, their death, and everything in between. The main goal is to help them find peace in how they died.
Part-horror, due to how outrageously terrifying some of the ghosts look, and part-comedy, due to the hilarious dialogue between the different characters, Speed Dating for Ghosts is a game with a lot to offer. Just one look at some of the potential ghost flings is enough to cause most people to cackle, and that is before considering the brilliant “bad date” scenarios available in the game.
5 Weird: Attack Helicopter Dating Simulator
If the idea of having a romantic evening with an Agusta Westland AW129 Mangusta attack chopper seems thrilling, then Attack Helicopter Dating Simulator should be a great time.
In this title, players join the airforce only to begin playfully flirting with the military-grade weaponry. Somehow, the game offers 11 different endings, allowing multiple playthroughs. This is quite possibly one of the most bizarre games in the entire Steam catalog.
4 Hilarious: Super Seducer
Aside from the controversy surrounding the game’s concept, Super Seducer executes it’s intended purpose in a ridiculously comedic way. Designed to train men into suave, smooth-talking gentlemen that can get any woman to fall head over heels for him, this game tasks players with guiding Richard La Ruina through a series of scenarios to pick up women.
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Pick the right choice, and you’re ever so closer to getting her phone number. However, choose one of the often absurd wrong options and prepare for rejection after heart-breaking rejection. If working on pick-up lines doesn’t suit one’s style, just boot this dating sim up to start arguments over why dogs are better than cats.
3 Weird: Doki Doki Literature Club
Initially, Doki Doki Literature Club is one of the most “normal” games on this list. As a new member of the literature club, the protagonist is engaged in conversations with 3 different girls each day. Each girl is seemingly completely normal, everything goes smoothly.
To avoid spoilers, let’s just say that the game takes a dramatic, disturbing turn for the worse. Doki Doki Literature Club becomes one of the most harrowing free-to-play experiences one can get on Steam. Whether that makes the game incredible, nightmarishly wicked, or both is up to the player to decide.
2 Hilarious: I Love You, Colonel Sanders!
Date Colonel Sanders. That’s it, that’s the game. Oh, and it’s completely free. Is there anything else that needs to be said? Commissioned by KFC, the player takes on the role of a culinary student seeking romance with their classmate, Colonel Sanders.
Participate in cooking battles, earn a fictional culinary degree, and make the Colonel your future business (or life) partner. Genuinely, this is one of the most hysterical dating sims available and the lovely folks at KFC are fantastic sports for blessing Steam with I Love You, Colonel Sanders!
1 Weird: Hatoful Boyfriend
Okay, so dragons, ghosts, attack helicopters, and Colonel Sanders don’t quite hit the mark. What else is there to do? Luckily, the men and women at Devolver Digital have the answer. As the only human invited to an all-birds school, you get to go to class and go on dates with pigeons. Yes, real pigeons. The ones that fly and are birds.
Such an insane, bizarre treat that is Hatoful Boyfriend has become famously known as one of the most worthwhile dating sim experiences out there. There is way too much to even begin to dig into this title, and if our ancestors knew we would be virtually dating pigeons in 2020, they would be appalled and confused.
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