It takes a special sort of person to look at jump-scare horror game Five Nights at Freddy's and think "romance." Luckily for you, if you're the sort who looked at Springtrap and thought "sweet sweet candy," someone has made the dating sim that can hook you up. Digital artist Chibixi created a flash game that started life as an April Fools' project, and has made her own cutesy anime-style art and three animatronics for you to romance with Five Nights of Love. OK, it's not a long play...but if you ever wanted to romance a creepy, homicidal animatronic, this is your chance.
You should also check out Chibixi's other work. Her dating sim for Thanksgiving food is a thing that happened, for sure.
If you've ever watched a male pigeon puffing up, cooing and dancing in front of a lady pigeon and sadly thought to yourself that you'd love to be romanced that way, you probably haven't yet played Hatoful Boyfriend (Steam link), the game where you're romanced by pigeons (also based on an April Fools' project). You're the only human student at a high school for pigeons, and you have to find love among the feathered denizens of the school halls. There's actually a very involved, post-apocalyptic sci-fi reason for this, which quite surprisingly brings some sort of sense to the whole thing.
You can find a Mac version here.
We know what it sounds like, but you're not trying to date your brother. You're trying to date a brother. A Brother printer, actually. The... er, literal object of your affections has transferred to your school, and you need to make it welcome with your love. And probably ink cartridges. This one actually seems to be made by Brother as a marketing move, in which case it's certainly one of the strangest we've ever seen. You can play it here, but it's Japanese-only and doesn't seem to work in the Chrome browser.
You won't be able to play PSP game Princess Arthur unless you go to or live in Japan and can read Japanese, but I would absolutely play an English translation if it were available. The premise: What if King Arthur (yes, that King Arthur) were a girl named Alu who became king against her will and then had to romance a bunch of knights and wizards and stuff, who are all anime-pretty. Technically, yes, they are human, but the concept is just so delightful. It was published in 2014, and the fact that it's never been made available outside of Japan is the real heartbreaker in this scenario.
Made in just two days for the Pulse-Pounding-Heart-Stopping Dating Sim Jam, Jurassic Heart will steal your heart with an adorable, shy character named Taira. Ironically, you are the one with the crush on this giant T. rex, and need to win his affection by taking him out to buy a new ukulele.
The game is a little on the short side, so if you want a bit more playtime (and a wide choice of dinosaurs to choose from), check out Dino Dearest.
Do you look at pictures of SlenderMan thinking he just needs someone to love him? Or feel that Jeff the Killer is simply misunderstood? Perhaps you need A Creepypasta Dating Sim in your life. In it, you can fall in love with one of six figures from creepypasta lore. It's not quite finished, but based on the demo (downloadable at the link), it's going to be a whole bunch of My Bloody Valentine fun.
Well, this one does exactly what it says on the tin. You seem to be the only human in a world of humanoid animals and demons, and the girl next door is literally a grasshopper, who you have to romance. The game was created by developer Nostalgia for the Nico Nico Jisaku indie games festival in Japan in 2013, and takes between half an hour and an hour to play through. If you want to play, you can download it here, and there's another version with a female protagonist here (Japanese only).
Benthic Love bills itself as "the original, critically acclaimed Anglerfish Dating Simulator," and it's true that we have never seen another anglerfish dating simulator before. The twist on this one is the way anglerfish mate. The male fish is absorbed by the female, becoming a parasitic appendage. She does all the hard work of swimming around and killing and eating, and he provides the necessary ingredients to make more anglerfish. So once anglerfish mate, they mate for life. You'll need to choose very carefully...
This one is a little on the risque side: You're an astronaut romancing your way through every intelligent species in the galaxy. Intergalactic Love Machine was made for a Ludum Dare game jam last year, and there are no two ways about it: you either seduce these aliens, or you're astronaut toast. Each alien has her own special likes and dislikes, and you have three lives to get it right. You are romancing for humanity! Make love, not blunders!
You can play it here, where you'll also find a version for Android.