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Dusk Raven
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends.
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.

Have Opinion, Will Write
I gotta say, I can understand it when a writer sets out to make two ponies a pair and manages to flesh out one or both of their personalities, but I don’t get it when people just ship Mane characters with apparently random background ponies.
 
I mean, it’s entirely possible from a realism standpoint that such characters might end up together, but what’s the context?
thps48
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
Wallet After Summer Sale -

Young Leosword
First I’ve seen of this shit. X3
 
If they have a relationship episode, what sit would be preferable: jerk-ass stallion or steady, recurring stallion? Double date wackiness from the latter, mind. ;D
GolemGear
The End wasn't The End - Found a new home after the great exodus of 2012

This ship came from the Ponibooru days, when people were trying to figure out a name for him.  
I forget what the ridiculously long name we came up for him as a compromise was, but it had something like “beard” and other such things in it.
FloydPinkerton

Three pictures in this ship were uploaded today, and there’s another from three weeks ago. They’re not all the same artist either. So this seems to be a thing.
FloydPinkerton

He’s a background pony who complains about the crappy cider. I think he’s a crowd-filler in other episodes too. Not sure if this ship has a name yet.
Twilight-Sparkle

No. It was somepony I was standing next to while Applejack was giving her speech before going to the rodeo competition in Canterlot. I have no idea who they are beyond that.