You could show him some SNOBOL. It's a string and pattern matching-based language that developed without all of the Unix history. It looks a little like FORTRAN but it is very much not. If he embraces it, he will get a very different appreciation for how regular expressions work that will be valuable.

I found learning Java you need an existing project that uses only a basic level of framework in unsurprising ways. My first Java exposure was to a Struts-based project with some considerably byzantine setup. My second Java exposure was to a Spring-based project and things made a lot more sense.

Wade.