The really funny ones have been listed already, but here are a few unusual ones I’ve played -
Katawa Shoujo - All girls have some kind of disability, as do you. It’s unique, and prepare for some deep feels, man.
Cupid - Available through itch.io here - instead of playing as the protagonist, you play as the voice in her head, “Mother”, who tries to manipulate her choices. Disturbing but brilliant.
Hate Plus/Analogue: A Hate Story - You can get them both on Steam. Super-cute robots, cultural archaeology, futuristic neofeminism, and a murder mystery to solve.
Asphyxia, or anything else by Ebi-Hime - (Available on Steam or itch.io) She writes dating sims that really aren’t - they’re not romantic, they’re usually depressing, and relationships almost never happen. This is one of the weirdest, where lesbian schoolgirls represent major Romantic-era poets.
Hustle Cat - (On Steam) The guys you can date in this game are sometimes cats. It’s more of a shapeshifting thing than a furry thing, but well, it can get weird.