I can’t think of a good general question and who to pick so if I can, I’ll go all of them ask ask for hugs~

Moondancer: What’s your favorite book?

Vinyl and Octavia: Which do you prefer…  
Vinyl: Dubstep…  
Octavia: or Classical?

Twilight: Hey CS, since Celestia loves you as her servant, would you mind being my servant too?
 
Celestia: Could you be a wonderful stallion and get some of these knots out of my back?

Twilight Sparkle: I have a copy of Daring Do and the Forbidden City of Clouds. Would you like to read with me?

And Rainbow would ask: If you had to choose between keeping your wings or your mane, which would you pick?

Rarity: Sir, I just made finished making a bunch of ruby-studded outfits. Would you like to have one?

@Celestia’s Servant  
PS: POnies asking ponies is also an idea I’m keeping in mind now^^

I say Blue Fast!

@Joshua  
@Jarkes
 
Simple:  
step 1: Pick a pony  
Step 2: Think of something it would ask me.

…I don’t actually know how these reverse rounds work.

Say, Moondancer, how is it going with your friends how?

I choose Sassy Saddles.