If you could...

[ravengusty]

...spend a day with any pony who would it be and why?

My boyfriend says Pinkie Pie coz she's mad as a hatter just like him.

I say SS Bouncy coz I reckon she'd be full of beans and help me keep fit hahaha

[Vintergatan]

One of the Pegasi so I could go flying with them! Wow, that would be awesome!

[Stiletto]

I would say Pink Pie too!  She is so random you can't help but just smile and laugh.  I need lots of laughter here recently, as life is kicking my butt!

[Sonata]

Oh man... I don't know ! D:

But I sure would love to spend a day with Pinkie and bake cakes and have a party !

On the other hand, Rarity could teach me all she knows about sewing ! That would be rad too~

[Ionn]

Twilight Sparkle. Sit inside a tree & read books about ponies all day? Check. Ask her 1001 annoying questions about everyday pony life? Check. Request a plethora of equally annoying magical examples? Checkity-check-checkcheck!

Or if I were feeling less introverted & had had too much sugar I'd want to hang out with the G1 baby ponies from those old comics. They seemed to get into the trippiest situations!

[Lady Starflower]

I first thought of Starflower cuz she's my favorite pony and being with a unicorn would be super cool! But then on second though Firefly or Rainbow Dash would be so fun to fly around with!

[Starshinescustoms]

Hmm, I'm not sure. That would be difficult. It would have to be a pegasus pony, because I'd love to fly with them 
I've always liked Wind Whistler and North Star.
I'd probably either go with G1 Firefly or G4 Rainbow Dash. Or maybe Spitfire! 
Edit:

But then on second though Firefly or Rainbow Dash would be so fun to fly around with!

You know what they say about great minds! 

[dxgirly]

Fluttershy! We could play with all the animals together!

[scarletjul]

I'd love to hang out with Wind Whistler, Twilight Sparkle or Paradise.  Wind Whistler and I could discuss logic, Twilight could tell me all about magic and Paradise and I could discuss pony lore and history. 

[Honeycomb]

Flying with a pegasus! Preferably Surprise or Honeycomb because they are my favourites.

[zzzova]

I would LOVE to hang out with some seaponies!! 

[Sakuyamon]

Luna or Twilight Sparkle, I wanna know everything about new and old Equestria and everything in between^^

[katrine2309]

Oh, it would have to be either Glory (because to me she is the most magical unicorn AND she is a fav) or Firefly. Because who wouldn't want to fly with Firefly?

[Tap Dancer]

One of the Pegasi so I could go flying with them! Wow, that would be awesome!

That's always been my thought! So I'd probably choose Firefly. Seriously, who wasn't jealous of Megan? LOL

[Jennifer2004]

I would love to go dancing through the clouds with Firefly! Just like Megan did in Rescue at Midnight Castle.

~Jennifer