Umm... arrows.

WYR kiss Puddleglum or dragon-Eustace?

Oh bother. 🙂 Eustace. 😀
WYR ride Eustace/Dragon or Fledge?

Fledge. 🙂

WYR journey with Cor and Aravis or with Jill and Eustace (SC)?

Cor and Aravis!!! :D:D:D
WYR hunt with a few a lot of other people?

A few of my closets companions. And I know who I'd pick! (We often joke that we four could fulfill the prophecy about the Pevensies. ;))

WYR play chess with Reepicheep or with Peter?

Reep!

WYR see hear Ramandu and his daughter sing or see the many white birds come and take the food from Aslan's Table away?

Oh man... I could choose Reep on the grounds that I have a small chance of winning (you know, if he were to send a knight out where it would go in a real battle...), but that hardly seems fair. Besides... Peter = favourite character. 😀 So Peter.

WYR fight beside Oreius or Glenstorm?

Oreius, I think. 😀

(Here, I'll use Ela's question since it got skipped.) WYR see hear Ramandu and his daughter sing or see the many white birds come and take the food from Aslan's Table away?

Hear the singing.

WYR have a gold or silver crown?

Uhh, personally, gold. 😛

WYR be a Telmarine or a Calormene?

Telmarine. Calormen is way too hot and sophisticated and Tash-y for me.

WYR get the silver apple out of the garden or *cough* collect the seven swords of the seven lords?

Oooh, I think I'll have to go with collecting the seven swords.

WYR spend a week learning about Telmarine customs (provided that they didn't kill you) or learn about giant customs (provided that it was not Autumn and they were not going to eat you.)

I think if my safety was guaranteed either way, I'd go with giants. My tall giraffeyness wouldn't stand out as much that way. 😛

WYR meet a talking squirrel or a centaur?

Centaur.

Would you rather live in a tree or in a cave?

Tree.

WYR be given a sword or a bow from Father Christmas?