...would be Miko and Tsukiko from The Order of the Stick. I don't know where this came from, but it could have been cute. In a creepy and disturbing sort of way.

So, in The Door Within trilogy (spoilers ahead, by the way, but I don't think they're too horrible), from which I take my screen name, there are two universes: Earth, and the Realm. Earth is, well, Earth, and the Realm is a parallel universe populated by what are known as Glimpses. Each Glimpse has a human twin who looks just like them and shares their beliefs/allegiances, though they may not be the same age (to steal the explanation straight from Wikipedia/The Door Within Wiki, don't remember which). The main characters are human teenagers who are allowed to go to the Realm for a while to serve the King (this is Christian YA, btw). When a human goes to the Realm, their Glimpse twin goes to Earth, so they never meet. Now that the explanation is out of the way, the ships...

Aidan Thomas/Gwenne. Aidan is the main character of the first book, and Gwenne is his closest friend in the Realm. They're an adorable couple. But...

Antoinette/Kern. Antoinette is Gwenne's human twin, and Kern is the Glimpse twin of Robby, Aidan's friend. He's also an evil knight who nearly killed Antoinette in a duel. Oh, and he's third in command to Satan himself. Yet also...

Antioinette/Aelic. Aelic is Aidan's Glimpse. But I don't ship Antionette/Aidan; ask thou not how the heck this doth work. To further complicate matters...

Robby/Trenna. Trenna is a Glimpse, and we never see her human twin. These two are also adorable.

So basically, I'm stuck with a huge mess of Glimpses and humans and it's all very messed up. Help.

-Alleb

Well, let's see, there's really no pairings in Homestuck that I can't be convinced to ship. I've seen, oh, GamzeeFeferi, GamzeeRose, and I once read a very very good fic where the main ship was the Condesce c3
Also, IDK how weird this is, but DipperPacifica

Well, let's see, there's really no pairings in Homestuck that I can't be convinced to ship. I've seen, oh, Gamzee<>Feferi, Gamzee<3Feferi, Nepeta<3Rose, and I once read a very very good fic where the main ship was the Condesce c3< Snowman c3< Alpha Rose.

Also, IDK how weird this is, but Dipper<>Pacifica<3/<3

Well, let's see, there's really no pairings in Homestuck that I can't be convinced to ship. I've seen, oh, Gamzee<>Feferi, Gamzee<3Feferi, Nepeta<3Rose, and I once read a very very good fic where the main ship was the Condesce c3< Snowman c3< Alpha Rose.

Also, IDK how weird this is, but Dipper<>Pacifica<3/<3

Just the ones I could think of off the top of my head:
--
Milton Fauster/Zayne (Heck: Where the Bad Kids Go): Because the Milton-Marlo body swap yielded too few ridiculous gay-ish moments. What if Zayne was only being nice to Marlo because he thought she was Milton?

Oscar Wilde/William Shakespeare (historical figures): Because angsty gay poets need to stick together (Shakespeare was bi. Fight me). I feel like their sensibilities were similar enough that they'd hit it off brilliantly if they ever met. . . which would be flat-out impossible. Without a time machine.

Gerard Way (lead singer of My Chemical Romance)/L (anime detective from Death Note): Because they would be great together. Also, a ship name generator said that their ship name would be "Lard." I toyed with writing a fic about this for a while -- I think I could actually get their worlds to intersect, either by using G's cartoon alter ego Party Poison, or a fever dream.
--
I've always been afraid to write fanfic because I thought I might break something.

Bowyer/Tailor (an obscure Flash game called Swords And Potions 2): Look, I have a thing for redheads, alright? And they're cute together. They're really, really, really cute together. =]

Grave Robber/Arbalest (Darkest Dungeon): Clinging to each other as they cling to life within the Stygian pits of once-fair countryside, rendered fouler than conceivable by the greed and madness of our Ancestor. This one also has the benefit of being canon... ish. The Grave Robber tells everyone they look hot, regardless of gender, and the Arbalest has the most attractive design in the game. By my very specific standards, anyway. =]

Hellion/Plague Doctor (Darkest Dungeon again): This one is... less canon. However, I think there's something intensely erotic about a drunken, halberd-wielding barbarian submitting to a skinny, nerdy girl with a penchant for medical experiments. As the meme says:-

Plague Doctor: *holds up a couple handfuls of leeches* i s2g im licensed

Loki and Maddy form Runemarks sound like a weird ship, but actually it's pretty much the only ship in our tiny fandom. (Although it gets weirder the more you think about it)

Occoo/Link (LoZ: Twilight Princess). I don't really understand why everyone I see play the game hates Occoo. And everyone ships Link with Midna.

Darth Maul x Disney. He's ducking back. Again. Someone need to introduce the guys phantasming about him in the scenarists team with the business end of a shotgun.

And I dunno whether that even counts as a weird ship, but I kinda ship Justice of Toren/Lieutenant Awn. Kinda.

I'd say the weirdest one is Anghel/Okosan from Hatoful Boyfriend. Mostly weird because birds, and because they're the two weirdest birds in the whole game.
A question remains unanswered: Why isn't anyone else shipping it? It's almost canon in the epilogue!

Arthur (from "The Girl in the Fireplace") and Susan ("A Town Called Mercy").

If you know who they are you'll know why it's funny. :P

But you cannot ship without this tune...

As seen in my very first mission, I entertained Neo (The Matrix)/Chell (Portal) for a time. I always thought the two of them were quite similar, being protagonists in a dystopian world who rose up against artificial antagonists and all that. Even though there's no way a merger between their respective worlds would make sense at all.

I also once shipped Dash Parr (The Incredibles)/Vanellope von Schweetz (Wreck-It Ralph). Which kinda proves that I love Disney/Pixar a little too much. XD