I have pretty flat feet according to my doctor, so I don't think flats would kill me too much. If they do, I guess I could get arch support insoles or something?

It'll take A LOT more practice for me to be able to walk properly and be comfortable in high heels.

Definitely walk around the house and break them in first. The first time I wore heels, I wore 3 inch pointy-toed pumps to a party. I felt fine, but when I took them off, the pain was excruciating. I ended up taking my shoes off and sticking my feet in the hot tub haha, they hurt sooooo bad ): the pain lasted for at least 2 days. ;;

Just be sure to break them in properly and practice in front of a mirror. There's nothing attractive about a girl who's up on high heels and looks like she's about to fall over every time she takes a step.

There are some inserts that are just like a cushion on the entire sole of the shoe. I've never tried them because even if I wanted them I was too poor so I just had to learn how to become more adept with heels. xD now I'm just really good with them. I wear them so often just to go around for no real reason that I've learned how much distance I can talk in them before the pressure builds up too much, how to walk, what kind of heels I like, and all that good stuff.

Oh. And BREAK THEM IN. The first week you wear them is going to be much different than the second. lol.

Um. Carry band-aids. A spare pair of shoes, just incase. . . Don't walk more than you need to. . . all of the obvious/already said things.

^.- You'll be fine. There's no magic to heels.