I want to copy the twitter profile page and have a url with a username "http://www.my-app.com/username" and while I can manually type this into the address bar and navigate to the profile page I can't link to the custom URL.
I think the problem is in the routes - here's the code in my routes.rb
map.connect '/:username', :controller => 'users', :action => 'show'
Also, I have Question and Answer models and I want to link to them with the customized URL like so:
http://www.my-app.com/username/question/answer/2210
There's nothing wrong with your route. Just remember to define it at the end, after defining all other routes. I would also recommend using RESTful routes and only if you want to have better looking URLs use named routes. Don't use map.connect. Here's some good reading about Rails routes.
Here's how this could look:
map.resources :questions, :path_prefix => '/:username' do |question|
  question.resources :answers
end
map.resources :users
map.user '/:username', :controller => 'users', :action => 'show'
Just a draft you can extend.
To create urls you need to define to_param method for your user model (read here). 
class User < ActiveRecord::Base
  def to_param 
    username
  end
end
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