I don't know if this might be useful for people, but I made this Pony Pairing generator. It has a list of over 300 characters, including plenty of background characters, a few Rule 63 versions, OCs, etc. And it will give you random pairings of them.

Here it is:
http://ponypairing.ucoz.com/pones.html

Here are some example ships it's given me:

Demon Sunset Shimmer x Sunshower Raindrops
Dusk Shine (Rule 63 Twilight Sparkle) x Lyra Heartstrings
Soarin x Aloe
Lady Tirek (Rule 63 Lord Tirek) x Pinkie Pie
Gummy x Sweetie Belle
Thunderlane x Boneless
Filthy Rich x Elizabeak
Snips x Daisy
Photo Finish x The Tree of Harmony

I got:

Lotus/Uncle Orange
Woona/Mr. Waddles
Noteworthy/Lickity-Split
Golden Delicious/Elusive

and...

Scootaloo/Bulk.

...This thing is starting to creep me out.

4270919 good lord this thing is hilarious!

I got:
Princess Sterling X Berry Pinch

Crazy Twilight X Boysenberry

Filly Twilight (Twily) X Twist

Sunny Daze X Peachy Pie

Hatchling Spike X Featherweight

Filly Twily X Sunny Daze

Babysitter Cadence X Filly Pinkie

Crazy Twilight X Sirocca

Filly Dash X Rumble

Princess Cadence X Pumpkin Cake

Princess Chrysalis X Zipporwhill

Zipporwhill X Filly Fluttershy

Auizohtle X Filly Celestia

Babysitter Cadence X Woona

Filly Celestia X Filly Fluttershy

Let's see, I got...

Octavia with Davenport (that could work, maybe)

Bulk Biceps with King Sombra (this must be done!)

Sham (R32 Flam) with Flim (that... definitely has potential!)

Mayor Mare with Caramel (hmmmm... maybe as a clopfic or something)

Cherry Jubilee with Cheese Sandwich (same as above)

Night Light and Princess Cadence (okay, I KNOW there's artwork of these two already!)

Actually, this isn't a bad generator. lot of names were hard to recognize (which one is Claude?!), but I can see this helping to make crazy pairings for authors as a challenge.

4270974 Claude is the puppet show guy from Inspiration Manifestation. This guy:

All the characters have a link to derpibooru, though it might not always work. Some of the characters have multiple fan names. When in doubt, I've tended to use the names from mlp.wikia.com's lists of ponies.

Silver Spoon and Future Twilight - I think Sir Barton hinted at this ship in An Apple Studded Diamond. It helps that Silver was Twilight's secretary and the story was set in the future.

Normal Norman (EQG) and Raven (Mayor's assistant) - personally, I'd make this either EQG or pony, but folks can do whatever they want.

Ace x Starlight Glimmer - poor Ace will never win another tennis match as long as he lives.

Elizabeak x Sapphire Shores - ummm... Serves Her Right?

Green Cycle (EQG) x Future Twilight - Flash Sentry would be so jelly.

Twilight Sparkle x Star Swirl the Bearded - There are surprisingly few stories about this one. We all know Twilight would if she could... well, maybe not in the Time Loop Trilogy, but...

4270951

Luna x Mr. Waddles has actually been done... Woona on the other hand...

Tinkering with things a bit...

Greedy Spike and Sugar Belle-Could be done, maybe Spike didn't recover himself and ended up on the edges of Equestria and is somehow befriended by the baker...

Philomena and Night Light-Suddenly, Twilight's Firey other form would make more sense...

Boneless and Aunt Orange- I could only see this as a clopfic, especially since Boneless' species is 'toy'

Barbara and Filly Rainbow Dash- Huh...okay, could be a cute fluffy piece

Stephen Magnet and The Mane-iac- HAH!

Matilda and Crazy Twilight- Crazy Twilight goes Crazy and Hedonistic with power over her new territory

This is kinda cool, just wish we could add or remove characters at our leisure (Remove some characters or add crossovers into the mix)

4271199

This is kinda cool, just wish we could add or remove characters at our leisure (Remove some characters or add crossovers into the mix)

If you download and save these two files to a folder on your local computer:

http://ponypairing.ucoz.com/pones.html
http://ponypairing.ucoz.com/pones.js

They need to be in the same folder as each other. You should be able to edit pones.js in a text editor (e.g. Notepad — not a word processor like Microsoft Word though!) to add and remove characters, then if you double click on the pones.html file it should open in your web browser and it will read your local copy of pones.js.

The basic format for a character is:

{
"tags" : [
"Princess"
],
"family" : "Royal",
"gender" : "f",
"age" : "adult",
"kind" : "Alicorn",
"self" : [
"Princess Celestia",
"Molestia",
"Trollestia",
"Prince Celestro",
"Tia"
],
"name" : "Princess Celestia"
},

The "tags" bit is used for various purposes like a tag of "OC" can be used to filter out OCs, etc. Just scroll through the file and you'll see what tags are in use. The "family" is optional; if two ponies have the same family, then they'll be considered an incestuous pairing. Similarly, "self" is used to detect selfcestuous pairings.

Zippoorwhill 63 x Applejack (this would be a fun one to see happen)

Dinky Hooves x Rainbow Blaze (Well, I do sort of ship Rainbow Dash with Dinky, so I'd be interested)

Pipsqueak x Spitfire (Interesting...)

Rarity x Littlepip (Ha! That would be a good one)

Nurse Redheart x Scooteroll (I don't have a comment, but I'd love to see this)

Noi x Zippoorwhill (Sounds like an adorable fic in the making)

Party Favor x Bloo (Well, I guess this would be fun, though I'm sure Trixie would kick him senseless, seeing as I have Bloo as her little sis)

Nurse Snowheart x Dinky Hooves (Why can I see this being very one sided? Like Snowheart is in love with Dinky, but it's mostly in secret)

Zippoorwhill x Twily (Just like ZippoorNoi, this would be adorable)

Octavia x Lily Dache (I may have had thoughts about shipping Silver Spoon with Octy once or twice, so this is something I'm fine with)

Vinyl Scratch x Homage (Yes please! <3)

Scootaloo x Littlepip (Hmm...talk about awkward, but fun~)

Ruby Pinch x Twilight Velvet (Hehehe, now that is my second favorite filly shipped with Twi's mom, Dinky was the first, now if Twi walked in all the three of them, especially with the fillies as colts...)

This is a nice generator, though it feels a little barebones as you can't specify who you want to be rule 63'd or not and a few other things.

4271417 The only ones that I've specifically put Rule 63 variants of are the ponies that seem to have fairly widely established gender swapped names, such as Twilight Sparkle / Dusk Shine.

There's no law that says you have to run the generator and write about the exact pair it gives you. If you see a pair and it starts you thinking that would be awesome, if only X was a little younger, and Y was a little older and female then it's done its job.

4270919 4270951 4270958 4270974 4271165 4271199 4271417
Here what I got
King AspenxCelestia
GildaxBlueblood:
I can see a story of this ship similar the movie, The Emperor's New Groove Blueblood get transform into a Griffon and wake up in the Griffon Kingdom and in a Rio-style Blueblood wind-up traveling with Gilda and she think Blueblood is a crazy Griffon who think he is a pony prince.
TirekxCelestia
Grogar, pic2 XTwilight:
Before the event current of MLP Tambelon and Equestria is having their first diplomatic meeting to build a peaceful relations between the two kingdoms. Celestia and the current ruler of Tambelon is having trouble finding a peaceful solution so to build a relation between the kingdoms so Celestia promised him that
his descendant will be wed to a princess if he agree to form an alliance with Equestria. Now in the current time after Twilight recently becomces a alicorn princess now Tambelon's current ruler, Grogar show up in Equestria for a meeting for the arrangement that Celestia promised his ancestor so being the only available princess Celestia
choose Twilight to be Grogar's bride but first Twilight have to meet Grogar so Celestia set up a arrangement for Twilight to sit in her meeting while she is negotiating the the peace treaty of Tambelon and Equestria with the ambassadors with Twilight being completely unaware that she is meeting her future husband. When Grogar first saw Twilight it was love at first sight and while Celestia is negotiating Twilight is get
to know Grogar and despite his scaredy appearance and his creepy magic aura he was very civil and polite and acting like a gentleman to twli and Grogar been doing this on for every meeting. And finally one day at a meeting Celestia announce that Twilight will be wed to Grogar as part of their treaty and after just hearing this Twilight reluctantly went through with it and Twilight will have to lives with Grogar in his
Kingdom Tambelon as his Queen and Spike went with Twilight and while living in her new home she see how different Tambelon is from Equestria but she manages after Grogar show Twilight his library. The rest of the story can be similar to a mix of Beauty and the Beast and the story Bride Of Discord.
SombraXTirek
Queen Haydon,pic2Xking Aspen
Queen HaydonxSombra
King AspenXZecora
BramlexBelle
age up!BramblexZecora
Fizzle,pic2xGarble
Sonata Dusk(in siren form)xTwilight or Spike
ScorpanxCelestia
Iron WillxZecora
BramlexSpike
King AspenxSombra
SpikexMina
MinaxMane-iac
Mane-iacxQueen Chrysalis
Mane-iacxSombra
R63!ZecoraxR63!Iron Will
Lady TirekxShining Armor
Princess AmorexSombra
R63!ChrysalisxShining Armor
R63!ChrysalisxPrince Cadance
Queen ChrysalisxPrincess Cadance
Princess AmorexKing Aspen
Princess AmorexShining Armor
R63!Princess AmorexLady Tirek
Princess AmorexLord Tirek
ErisxSombra
R63!ChrysalisxEris

I decided to do six random pairings. I excluded non-pony species, Rule 63 ponies, OCs, and Equestria Girls characters. Here's what I got:

1. Sapphire Shores x Raven - I didn't have a clue who Raven was until I clicked on her derpibooru link. This would be one weird crack ship. Raven looks like some sort of intern.

2. Princess Luna x Flutterbat - Okay, this one would be fun. Maybe Flutterbat could even be Luna's personal guard?

3. Featherweight x Liza Doolots - Once again, had to click Liza's derpibooru link to figure out who she was. They look like they would be a cute couple actually.

4. Cloud Chaser x Open Skies - One character I've seen multiple times, the other I've only seen in one episode. Based on looks, they would be an...interesting couple to say the least.

5. Maud Pie x Toe Tapper - When I clicked on Toe Tapper's derpibooru link, I almost instantly thought that this would be an unusual couple. Musical and emotionless...hm.

6. Crazy Twilight x Blaze - I honestly don't know what to say about this one. I feel...indifferent.

Darn it all why did I choose to exclude non-pony species if I hadn't done that I would have probably gotten Applejack x Discord Uh um I mean that was fun to do the pairings were unexpected YAY CRACK SHIPS

This thread had been necro'd?

Well, first one I got today was Rainbow Dash and Twilight Velvet... I actually remember a story where Twilight and RD have a contest to see who can write the better shipfic... and Rainbow ends up writing a self-insert where she makes out with Daring Do. Twilight tells Rainbow that Daring Do is (this was written pre-Daring Don't) written by her mom, and that it's almost like she wrote a story with RD making out with Twilight Velvet. Dash's response was something like... "Yeah... so?"

Second one... Adagio Dazzle and Berryshine (Berry Punch). I'd almost pay to see that one.

Third... Pipsqueak and Nyx? In a convoluted sort of way, it almost makes sense. Pip said Luna was his favorite princess and probably has a fetish for alicorns (consider his two appearances - Luna Eclipsed and Twilight Time). Nyx was created from the essence of Nighmare Moon and Twilight Sparkle's blood in a botched spell. It does kind of make me wonder whose OCs and how many are in this generator, though.

4270919 Tennis Match is in it! I love you!

4458303 How could I not have included her? She's one of the pivotal characters of the show!

Actually I don't think she was in my initial release, but I included a bunch of background humans in the first update.

4458316 Awesome-sauce!