If you put aside 'web', I imagine Python to be the best training language - its the new Pascal. I say that as one of the European Turbo Pascal generation that used TP as a stepping stone to assembler. Python offers that same clarity without the dumbing down. Python is as close to pseudo-code as I've seen. Its what I imagine myself introducing my children too just as soon as a I dare let them borrow my computers...
But if he really means web, Haxe might be a good choice. Its javascript-esque, it runs in browsers, and you can do fancy graphics and games and such. I imgaine making flash applets to be far closer to what he might enjoy rather than text-based stuff that more classic web development generates.
The whole making web pages and equating that to programming - sure its a job and all, but is it fun and inspiring?
it doesn't have to be about community.
In terms of more academically interesting languages, I might recommend Haskell or Clojure.
Rails for Zombie could be a good starting point.
Side note, when I say I am new to programming, 3 months ago I barely knew what css ment - and have never taken a cs class.
* the basics - http://www.codecademy.com/#!/exercise/0
* more advanced - http://ejohn.org/apps/learn/
1: More established languages tend to have far more documentation, tutorials and example code.
2: More people use more established languages, so asking for help tends to be a lot easier.
3: Programmers can be a prickly bunch, and it is quite likely that beginners will realise this as soon as they try to explain why they're writing an RPG in Python rather than <insert somebody's favourite language here>.
4: A lot of the attraction of 'easier' languages like Python is that they take the boiler-plate code that other languages require and hide it behind a nice friendly syntax. This is very useful for programmers who already understand the concepts that are being glossed over by the shiny syntax, but beginners may struggle to comprehend their own bugs / problems, or even explain them to others if they do not understand exactly how their language of choice is helping them by cutting out the boiler-plate.
All that being said - there are much worse places to start than Python. I would just recommend that learning a 'harder' language in tandem may be very useful to beginners.
If we're talking web-app specific stuff here - Ruby on Rails is quick and easy to get something nice up and running quickly. Ruby is somewhat similar to Python, too.
Happy hacking.
