I was wondering if anyone had any guilty pleasure pairings out there that are either hard to justify or just outright odd. If you could provide any background or any explanation, go for it!

For example, ever since playing the Subspace Emissary in Super Smash Bros. Brawl, I've unironically shipped Samus Aran and Pikachu, even though I could easily see why that wouldn't work on so many levels. I found the taboo on top of the whole "stoic, fearless bounty hunter, and her little pet mouse" to be a cute combo that has it's share of fans.

I'm trying to think of similar pairings that I had in the past, but none are coming to me right now. If any responses spark any memories of such sin, I'll be happy to add~

Other than various incest ships e.g. Koopalings I don't really have any "weird" ships per se.

I'm a Homestuck, so not only do I make weird ships, I have multiple kinds of shipping.

Anyway, I've shipped Augustus from Bttersweet Candy Bowl with a cupcake. It is an inanimate, non-living, non-sentient cupcake.

I don't see what I do as shipping because I don't have particularly strong fixations to specific fantasy characters. I certainly am not interested in matchmaking with no self-insert element. Calling what I do "shipping" is a mischaracterization and limiting.

I will, however, pair anyone with anyone and imagine their mini-story--freestyle shipping, if you will--as long as I have relatable art of them that kindles desire. Sometimes they're helpfully in the same art, so I only need to add some preferred context before and after. Sometimes, I will look up a character or franchise to perhaps clue me into what an artist was attempting to convey. Other times, when considering art not featuring my gender (or where available same-gender characters seem unrelatable), I will search art I've already decided to keep for a suitable avatar and combine the characters into the same scenario.

Not only do I look for art I find potent, but I also look for in art suggestions of story or characters with non-generic personalities, even the barest hints are workable. Similarly, a character or concept I find unusual can pose enough of a challenge that further stimulus is unnecessary (e.g., post #1444176 novel coming out this summer!).