TextMate is an editor and not a full-blown IDE, so it doesn't support debugging.
If you're looking for a Ruby IDE, I highly recommend RubyMine. It's got great support for debugging, running tests, easily navigating between files, and basic refactoring. Admittedly it's a lot more heavyweight, so I tend to use it for major work (or when getting up to speed on an existing code base), and still use TextMate for quick changes.
There are some open source solutions as well. In the past I've used NetBeans and RadRails, and particularly NetBeans has worked very well for me, too. Not as good as RubyMine, but well worth checking out if you're on a budget.
I should also point out that you can debug Ruby apps from the command line, using the ruby-debug
gem. Basically, you place a debugger
call into your code to set a breakpoint, and then run the app with rdebug
instead of ruby
. Check out this article for an overview.