To be fair though, this is far from the weirdest dating sim I've ever seen. I must say, my personal favourite is Hatoful Boyfriend... A kind of harem anime game, where you play as the only girl in an all boy's school... For pigeons... You heard that right. A pigeon dating sim! (Just want to clarify here that you yourself are not a pigeon because, you know, that would be weird! You are, in fact, a human girl who's goal is to find romance with one of many talking pigeons.)
There's a dedicated childhood friend pigeon, a snobby French exchange student pigeon, a popular flirty jock pigeon, a sexy teacher pigeon... And I think there might've been a ghost pigeon in there somewhere, because just being a regular talking pigeon wasn't weird enough... And they're all so dreamy! However will you choose? ^_^
… I also hear there's a dating sim where you get to pork a T-Rex or something?