I made a cake for my sister's wedding last night (groom's cake) and I had to wrap the cake 6 times before I "kind of" got it right! It was horrible. It was my first time wrapping a cake with fondant and it kept pleating on the sides and looked ugly. I've watch tutorials and they make it look so easy. How do I get it to wrap nicely and look pretty and clean? 

It takes practice hon:)   As the fondant falls down the sides of the cake you just lightly pull it away from the cake and smooth it out & down with your hand.   You don't say how big the cake was but of course the larger the cake, the larger the piece of fondant you have to use so it's more trouble to work quickly.    Hope that helps you some.

You have to make sure you've rolled it out to a size larger than the diameter plus the height of both sides combined.  If you try to skimp on the amount of fondant and only use what you think you need to cover it, there won't be enough excess to smooth out pleats (I've made that mistake before).  There will almost alwasy be pleating at the bottom, just like a flowy skirt or curtain hangs.  So you need enough excess fondant (about 2 inches all around) to smooth the pleats down into the part that will be trimmed off.  Like kakeladi said, the larger the cake, the more difficult this is.

That is interesting. I actually find it harder the smaller the cake is... Pulling it away from the cake helps. Chilling the iced cake before covering it helps too. And use a fondant smoother next time, it's worth the few $!

I am so with you on this one. I can do a lot of things but cover a cake completely in fondant is not one of them!