Usagi/Serena like Pinkie is all about fun, high-energy, and can be silly but is growing into a more mature person/pony as the show progresses. Usagi learns to be less flighty and less of a crybaby as opposed to how she acted at the beginning of the show, Pinkie learns in Too Many Pinkies that she is not a nonstop party machine (showing that she might have seen herself the same way her friends did). Both still retain a bit of their childish nature, but learn that there is more to life than constant fun/frivilous things.
 
Rei like Rarity comes off as selfish/vain, even materialistic at first, but can be very generous. Both aspire to greatness, and have artistic talents. Rei is interested in pop culture in the same way that Rarity has a fascination with the Canterlot elite.
 
Ami like Fluttershy is quiet, reserved and prefers the company of books/woodland critters to human/pony interaction but will defend her friends when necessary.
 
Makoto/Lina like Apple Jack, besides being a tomboy, is a hard-worker, both are physically strong but can be gentle, as well as having strong/independent personalities. Not to mention both lost their parents at a young age.
 
Minako/Mina like Rainbow Dash is athletic, resilient and clever. Both are cheerful, and romantics (Minako being boy-crazy, Rainbow having a romanticized idea of the Wonderbolts, could be indicated by the lyric “Perform for crowds of thousands, they’ll shower us with diamonds” in Best Night Ever). Plus both are known for being overly-ambitious.

@Background Pony  
Chibi-Usa = Princess Skyla  
Tuxedo Mask = Flash Sentry  
Queen Serenity = Princess Celestia  
Queel Beryl = Nightmare Moon  
Luna (Usagi’s cat, not Princess Luna) = Spike

@Background Pony  
Her minions have minions now. She has no need for inferior apish sub-minions.

Sailor Saturn for Twilight. They can discuss how each one deals with having enough power to literally destroy the whole damn world.

alicorn twilight = eternal sailor moon

I like this. Now for the shipping~ I kind of like it.

Where is Chibi-Usa to give Twilight some love?

Cool pic. Arguments could be made about the pairings, but overall, very nice. I like Sailor Jupiter and Applejack. Strong tomboy’s who are (or have a desire to be) very domestic.

Cool pic. Arguments could be made about the pairings, but overall, very nice.

@Background Pony  
I would say Amy would be a better fit, you know how both love to read.

@Prof.NightJack  
Okay, she’s split between the two.

@Background Pony  
But Serena is with Pinkie.

@Background Pony  
No, she has Serena.

twilight forever alone?

I can’t help but think Rei and Rarity are the worst to put together…  
I don’t know why.