@mathprofbrony  
Pretty good ideas, though I think Rainbow Dash would have a better time with Yang. Both Ruby and Rainbow are fast little speedsters, Yang’s competitive, thrill-seeking attitude gels better with Rainbow Dash in my opinion. Also the ‘what about a cute little pony’ comment that Yang made in the initiation.
 
As for Twilight, I personally wouldn’t pair her with Glinda. Mostly because I would think it best to compare Mane characters to main characters (RWBY + JNPR). Personally I can see Blake and Twilight getting along. If nothing else, they both love to read.

Ruby and Fluttershy would get along swimmingly.
 
Let’s see. Who would be besties?
 
Everybody lumps Pinkie Pie and Nora. Which works, so it’s fine. Ditto Weiss and Rarity; lots in common.
 
Ruby, otoh, seems more of a Rainbow Dash type to me. Small, fast, talks a mile a minute. She’d still be friendly to Fluttershy, she knows how to be diplomatic. However, she and Blake would probably get along better. Blake’s quieter, and knows about wanting to hide your face. If Blake takes umbrage at being linked with the animal lover I’d go with Ren.
 
Applejack strikes me as very Pyrrha. Down-to-earth, competent, dependable.
 
Twilight would probably like studying with Glinda, to learn about the local magic.
 
And, of course, Celestia/Ozpin. Because “your landing strategy is up to you” is totally a thing Celestia would say as she tosses Twilight, physically, at the latest problem facing Equestria.

As a fan of RWBY, I approve of this.