Beginner Help -- Txt game

Last time I posted here I was delightfully surprised at the

assistance I got. I made a text game on my TI-83+ in high school and
figured it would be a good learning experience to recreate that in ruby.
I figured I could expand quite a bit from a calculator. I own both
“Programming Ruby: From Beginner to Professional” and the Pickaxe. I’ve
reached a point where things are just way to messy and decided I was
going to redo the whole thing. Problem is I cant really find a better
way to do it. I am hoping to get some suggestions on general technique
as well. I really need to find some sort of guide about commenting to,
as you can tell.