Have you thought about IronPython, or one of the other "off beat" languages that run on .NET? If you already know C#, my guess is you probably know the .NET wi

Have you thought about IronPython, or one of the other "off beat" languages that run on .NET? If you already know C#, my guess is you probably know the .NET windowing libraries and perhaps are familiar with WPF. If you know those, you can pretty easily experiment with another language that's more expressive than C#, but still use the libraries you know. I'm not sure of the state of any of the other languages, but IronPython seems to be at a decent maturity level, and it's .NET implementation is actually faster than CPython in some cases. There's also IronRuby, but that project is still pretty green. You also have languages like L# (.NET implementation of Lisp) S# (same, but smalltalk) and F# (.NET ML) that are in various stages of readiness. I've heard rumors that MSFT wants to make F# a full fledged citizen of the .NET landscape. We'll see. I've also messed around with the new PowerShell scripting language. It's actually possible to access the WPF libraries from a shell script in Windows. That's kind of cool. I was considering making a Windows app based on PowerShell for a while there, so I looked into it for a few months.