I don't think it makes sense to start this endeavour by choosing a programming language. I think he should choose something he wants to develop, and then choos

I don't think it makes sense to start this endeavour by choosing a programming language. I think he should choose something he wants to develop, and then choose the programming language as a technology choice in the development of that project. If he wants to do web, Python/Ruby would be good choices. If he wants to do a native iPhone or OSX app, he should probably start by brushing up on his C then learn Objective-C. When you're programming, the biggest motivator for me isn't to learn a new programming language, it's to work on a new project, and being motivated is important. I always choose language as a tech choice of the project. YMMV