Spitfire, I like her attitude and how she presents herself to others. The Wonderbolt's part is nice but that's not all there is, Plus for some reason she comes off kinda like a cougar :X

I'd date/marry my mistress, The Great and Powerful Trixie!
I'm her loyal pet, but I'd be even happier if she was my girlfriend/waifu!

If gender swaps count, then it would definitely be Apple Jack, the stallion version. If not, then I guess it would be Big Mac or Blueblood.

I'd go for eithe the cougarish Miss Harshwhinney or the country gal who they thought was Miss Harshwhinney. I like thick country ladies with freckles but AJ just has a personality that's too big and brash.

For a stallion, I'd take Blueblood and do everything I could to change him.

I'd love to date Twilight or Fluttershy. :) Or Big Mac. :)

Twilight Sparkle, Trixie and Rainbow Dash. I hope mahogany is allowed.

I'm sure that those three won't really care what type of floor you have.

i choose twilight sparkle

Mare: Octavia or Apple Jack

Stallion: Big Mac

There's not enough love for Harpo/Parish Nadermane if you ask me. He is one handsome stallion, if I do say so myself, and he'd probably be a pleasantly surprising conversational partner. Among the less obscure ponies, I'm not quite certain. Twilie and Pinkie would be up there, naturally, but I suspect there would be more than a little polyamory going on. Fancypants is also pretty awesome, but bagging the most interesting stallion in Equestria could prove to be a challenge even in hypothetical thought. Ah well, the chase could be rather entertaining.