All right, so... think of the most completely bizarre, off-the-wall, unlikely, illogical pairing you can imagine, then write a brief summary of how the two could have possibly come to be romantically involved.
Example:
Mr. Carrot Cake and Princess Cadance
By the time Cadance's first anniversary rolls around, she's begun to grow distant from her husband Shining Armor, who's never at home due to the need to constantly travel between Canterlot and the Crystal Empire. When one of the confectioners from her catering service catches her eye while hubby's away, who knows what could happen...

958921
this thread is gonna be good

hold on let me come back in a bit

958921
DerpyXSombra

My actual entry is Luna X Bon Bon. Luna loves candy. Bon Bon loves Luna.

Actually, that one kinda makes sense, because candy=nightmare night.

Meh, still my OTP.

Princess Celestia's been cursed by me, Discord, into falling in love with... Well, need I say more?

You never said it needed to be canon.

Rarity and Tom.

After the events of her becoming Discorded, she realized that even though Tom is but a boring rock on the outside, he is a passionate soul on the inside. She gets Twilight to set a spell and Tom becomes a stallion and then they all lived happily ever after, the end, they all fucked, however you wanna say it.

Iron Will / Cheerilee.

Iron Will establishes a new entrepreneurship as a commercial spokesperson for a quick-time education program that Cheerilee views as a sham. She decides to confront him to challenge his teacher skills, and one thing after another...

958921 Discord and Cadence

Why? because DISCORD

958955 I've been rejected by her before... She said something about being married.

958945 Didn't Discord and Tia have a brief fling as kids before she rejected him causing him to turn into the discord we know today?

958959 Actually, I don't remember much of my childhood...

958965 well, who has the time? My brain's messed up on account of i was the result of love poison. Yes, the original. My mother was the princess, my father was the prince, but they were always changelings. history has a way of editing small details like that.

Sheriff Silverstar/Scootaloo

"You're my favorite deputy!"

Zoidberg and Rarity. Someone should write that.

The Friendship Express and the Train Tunnel to Canterlot. No, I've already written it.

But, if we're talking people characters, Celestia's pet phoenix Philomena needs to get with Owliscious.

Actually, that's kind of a good idea, so clearly it must be Rainbow Dash and Steven Magnet, the fashionable river snake. She crashes in the Everfree and then the two becomes friends again because they met once or something.

Iron Will X Pound Cake

I like to pair Twilight with Sombra, Discord, or Chrysalis in a teacher/student relationship. Like her thirst for knowledge led her down a dark path of no return.

Fluttershy with Iron Will makes for an interesting pairing as well. Iron Will is tamed by her gentle, inner strength. He finds something of the Dao in her. It's a little awkward for him, so no one he knows professionally is aware of it.

I'm not really sure if those are all that weird, though.

These are two I did a while back for prompts, but:

Spike X Celestia.

After Twilight dies, Harmony Day becomes a national holiday on the anniversary of her death. Over the centuries, most ponies forget why the day is special and even Luna and Cadance move on. Only Celestia and Spike continue to hold the vigil, and a relationship dawns from that.

Luna X Derpy X Macintosh

No one comes to the Court of the Night. Bored and lonely, Luna starts looking out on her country via her connection to the moon. She starts noticing Macintosh out there on a hill once a week and, one time, Derpy randomly shows up and starts writing a letter with reflective ribbon. Mac helps her out, and it turns out to be a thank you letter to Luna. Luna writes back using the moon, and over time Derpy and Mac form a relationship as the three keep exchanging letters. After a while, Derpy and Mac ask Luna to join them.

Twilight X Starswirl - just because she`s in her twenties and he`s been dead for centuries does not mean their age gap is unsurmountable. (No, I`m not talking about time travel here.)

Rarity X Iron Will - secretly, Rarity always wanted a man who can take the charge.

Fluttershy X Fluttershy - after Pinkie cloning disaster, Fluttershy realizes it`s a perfect opportunity to get with someone she can totally relate to.

Rainbow Dash X Tank - opposites attract. Need I say more?

Applejack X Discord - Discord is all about making the universe lie, and that angers Applejack each time she thinks about it... So why is she looking forward to experiencing it again? Guess mares do love bad boys after all.

Pinkie Pie X Octavia/Vinyl Scratch - as it turns out, Octavia IS Vinyl Scratch. And Pinkie is strangely attracted to that duality of a pony.

I wrote a Tank x Celestia ship a while ago that's on here. I'd like to think that doing so makes me quite an idiot.

They get together after a pet playdate, by the way.

rarity x r63 blueblood x spike

blueblood is sex slave

Pinkielestia

Summary: Celestia needs a pony to organize a party after her majordomo becomes ill. Who does she call? The best Party Planner in all of Equestria and a trusted friend who just wants to see everypony, including the implacably calm and secretly morose Solar Princess, smile.

RariLuna

Summary: Luna, ever the emotional and slightly batty Lunar Princess, comes across an article in Cosmotrotitan about "What it means to be a modern mare" and can't quite get all the concepts (she's a 1000 years removed, after all). She decides to call upon the one pony who is the living embodiment of the "spirit of the age".

DiscoDash:

Summary: After finally deciding to cement his heel face turn, Discord comes across the brash Pegasus while playing around in the Everfree. The two get into a contest where Discord loses cleanly. To "retaliate", he harmlessly pranks the fun-loving pegasus (say a gray-scale mane). The two take turns goofing with each other until they find more in common then anypony thought possible.

ScootaBloom (wait until they're grown up or make it sweet as hell).

Summary: finally got her cutie mark! However, the two remaining Crusaders can't seem to find an answer. The bonds of time seem to break the CMC apart until Sweetie becomes another face in the hall. Apple Bloom and Scootaloo continue to struggle to get their Cutie Marks, but along the way, they promise each other to never drift apart.

Fast forward a few years and both have their marks, but Scootaloo has to attend all the usual flight camps to get some sort of certification. But Apple Bloom misses her best friend and confidant horribly. Does the bonds of friendship mean more when distance is involved? And does the two childhood friends really know how the other feels?

FancyTrix (Fancy Pants)

Summary: The down on her luck unicorn is the unintentional pariah of Equestria. After twice falling before Twilight, she's the laughing stock of every town. While struggling to make a living in Canterlot, she happens across Fancy Pants. Being the good guy he is, he offers some assistance to the down on her luck conjurer to rehash her image and give her one more chance. Does his kindness skew her world view and can the philanthropist and play-boy fully understand her struggles?

That's all I got.

959016 Shouldn't you be working on a Nightglare moon fic

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I'm half planning an Octavia x Braeburn ship. They meet during a political event in Canterlot (he's there in a small role, she's there to perform), they bond over drinks, and it goes from there. Does that count?

I thought about making a oneshot Zecora x Blueblood romantic clop peice.

958952
You should leave it as just a Rock.

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Night"stare", and not until I finish a couple of things on my to-do list.

Such as replying to this comment. Next up, scratch head...

959186 NightGLARE.......Hint hint........

OctaviaxBig Macintosh
Octavia always likes a staliion who's strong, shy, and quiet. She also likes how refined he is despite coming from a country background. Big Macintosh thinks Octavia's music is beautiful and admits that he likes a classy mare.

959193
(Scratches head in confusion)

958921

Ms. Peachbottom x Princess Celestia

Let's say Celestia takes a hiatus from princess-ing, and decides to travel Equestria under disguise to get to know her ponies more. She takes the form of an Earth Pony for this, and begins hitchhiking from Ponyville. Here, she meets her traveling buddy Ms. Peachbottom. But how long will they be buddies?

959183 NO, TOM IS SPECIAL.

958921 Discintosh, Nightmare Cake, Chrysa-Tom

Gene Simmons and Rarity.
The fashionista attends a Kiss concert and harasses Gene into changing his attire. She quickly discovers how talented he really is.

Richard Simmons and Rainbow Dash
I don't even

Sonic x Lightning Dust.
Competitive angry sex. Lots of competitive angry sex.

959080
Twice as Bright has some well-written Pinkelestia.

I read a fic once that shipped Twilight/Flim. Also, i once almost wrote a fic shipping Spike/Hoity Toity.

El Presidente and

I have no justification for this. It just works on so many levels.

959554
When you say 'Nightmare Cake,' are you referring to a specific one of the Cakes, or does she just generally force herself upon the entire family?

960506 Good point. I forgot they all ended in Cake. I was thinking Carrot Cake.

959004

958921 The quill and a sofa from Quills and Sofas.

Rarity x blueblood

All backgroundxmain is a crack ship by definition.

Let's begin.
TwilightxRaindrops.
They met after Winter Wrap up and learned they shared the same passion for books and reading. One thing lead to another and Raindrop and Twilight share their first kiss.
ducky stahp, ure fujoshiing
Twilight keeps their relationship hidden from her friends but not because she is ashamed but because she is a silly pony who doesn't want to be teased. Raindrops doesn't mind but she'd like it if Twilight were to made it known and they sometimes bicker over this issue.

FluttershyxSea Swirl
Like Fluttershy, Sea Swirl likes animals, aquatic animals.
They start with a left hoof because of Fluttershy killing fish to feed her animals, but Sea Swirl realizes that Fluttershy doesn't kill them out of spite but because some of her animals need to eat fish to survive and that Fluttershy dislikes it just as much as her.

ChickadeexRainbow Dash
Although Rainbow only knew Chickadee as that strange pony that annoyed the living hell out of her and her friends, an incident which locked up them inside a small room sparked their relationship.

Double the dose for background random shipping.
RosexCloudkicker
Small talk during Cloudkicker's visits to Rose's shop made love crept inside. Now they are the hottest lesbians on Ponyville.

NoteworthyxVinyl Scratch
Disc store romance. They realize they like the same blues poni and Vinyl's pushy approach makes Noteworthy, who is a gentlecolt, to accept her advances, although unwillingly at first.

Golden HarvestxDizzy Twister
They are such silly ponies, eating carrots and stuff.
After Dizzy helps Golden out of an spider attack on Nightmare Night; Golden teaches Dizzy about the wonders of carrots and she falls in for the bad candy, so Dizzy is fished into a dysfunctional relationship with the irate Golden Harvest.
Before she realizes, Dizzy begins to reciprocate her feelings beyond carrots and tries to help Carrot with her temper with not so good results.

JunebugxAirheart
I just don't know. Airheart is yandere for Junebug since she gave her a basket of flowers on a gift exchange.
Junebug is scared of Airheart but being such a kind pony she gives in and accepts Airheart out of pity.
Sad sex everyday.

Haha oh wow.

959044
...That puts a WHOLE new spin on Just for Sidekicks. Me gusta!

My entry?

*slams down a hand of five aces*

Trixie/Squirrely.

She's an arrogant magician with a dark past. He's a flying squirrel whose mother always put his crappy pictures on the fridge in frames. Together, they fight crime!

And make sweet, sweet lovin's. To Barry White music. Because Barry.

Octavia x Fiddlesticks. They meet at some sort of music convention, immediately bicker over whether classical is better than country, have an epic music battle, etc. Over the course of the fiction, their passion for music develops into an entirely different kind of love.

Carrot and Cup Cake x Clyde and Sue Pie. The Cakes, who act very different behind closed doors, if you know what I mean , decide to give the straight-laced, prudish Pies a lesson in loosening up. Basically an excuse for swinging sex.

Flim x Trixie. The down-on-their-luck Flim Flam Brothers run into the equally-shamed Trixie - quite literally, when "Old Squeezy" crashes headlong into her new traveling stage. Arguments ensue. But Flim sees something special in the stage magician.

Celestia x Nightmare Moon. A particularly unique set of astrological phenomena brings about the return of Nightmare Moon. She still wants total domination and control of the Sun. But she's going to go about it in a slightly different (read: sexy) kind of way.

And I'm done.

959402
Exactly, He's special just the way he is.
It's just everyone else that can't accept Rarity's true love
"But it's just a Rock"
"You've never felt the way I have!!"

Pairings? Allow me:

Cherilee x Luna x Cadence: Alt Universe here where Cherilee comes from a long line of teachers who learned everything. Celestia placed her in Ponyville to keep an eye on Twilight and she sends Luna and Cadence to Cherilee to learn things.

Tom x Mane 6: NOO! They split Tom six ways and after a night of drinking and partying, things get out of hoof.

Vinyl Scratch x Luna x Octavia: Bored of life in the castle, Luna goes out and explores the Canterlot Club scene. Who should she meet besides a famous DJ and an equally famous cellist?