Awww, Lunatic, you beat me to it! XP I saw the topic for this thread and was like, "OH MY GOD I TOTALLY HAVE AN ADORABLE PICTURE OF FLUTTERSHY WITH EEVEES!! AAAAAAAAAH!!"
...Yeah.
Fluttershy and Eevee were pretty much made for each other. The combined adorability skyrockets off the charts.
I can imagine Pinkie Pie with the Haunter in the early anime of Pokemon. The one that plays tricks on people and laughs ALL THE TIME. Plus it's "supernatural", just like Pinkie's... sense... so I think that fits too. It'd also be such a Pinkie Pie thing to own a killer Pokemon that can EAT PEOPLE'S SOULS THROUGH THEIR DREEEEEEEEEEEEEAMS, and not even know it.
Pinkie: What? o_o He's dangerous? ...ARe you sure? Naw, he's just a big silly face!
Haunter: Haun-haun-haun-haun. *nod nod nod*
If we were playing off Rainbow Dash's actual pet (the turtle), I could see her with Squirtle, again the anime version. Those sunglasses, the attitude, the pranks... Yeeeeeeah. Plus, maybe Squirtle could help with gathering the water for Cloudsdale, or other various weather-related tasks.
Totally agree on Rarity and Milotic, though I think Meowth could fit (seeing parallels with Opal as well as both of their fascinations with precious materials), or Glameow, or even Persian.
Applejack and Growlithe, def a match made in heaven. It just seems natural for me for a praire girl to have a dog, and the fiery Growlithe seems the most appropriate.
Twilight Sparkle I can see really loving the psychic types. Maybe Gardevoir. So unassuming, yet actually incredibly powerful. ...I said that just to see how it would seem, but actually I'm loving the idea now! >w<
I feel like I want to draw all the ponies with Pokemon now, heehee!! >w< <3