Well, does he have an internet connection? If yes, you could direct him here, we're always glad to help. Let him introduce himself on this thread, too.
One thing beforehand: It's best to learn how to roleplay while sitting at the table with others. It's like learning how to drive: You have to really do it in order to really learn it. It's something you have to see for yourself. If not possible, of course we can try.
The link BiggusGeekus posted isn't bad, and I can also recommend the D&D basic game, which is meant for exactly that which you need: Introduce people into D&D. It contains everything you need to start up:
A Quick Start Guide with very simplified rules.
A first adventure to put players through
4 premade characters, using the very simplified rules
An advanced rulebook that picks up where the quick start guide left off (this is still not D&D, but is a little more complex than the quite simple quick start rules). This contains a Player's Handbook Lite, Dungeon Master's Guide Lite and a Monster Manual Lite. These rules have everything to play characters of 1st and 2nd levels, and don't contain all the races, weapons, skills, feats, or pieces of equipment yet, and only a handfull of monsters
But the D&D Basic game doesn't only contain rules, but some other material as well, stuff you can use even when you move on to real D&D
4 two-sided tiles (10"x10") with rooms painted on
A set of color-coded dice (nice thought, really. We all knew how we first were sort of bewildered by the different shapes of dice and had problems telling them apart. With these dice you can say: "roll a d20 - the orange one" and so on to help them on the way)
16 miniatures from the D&D Miniatures line. This includes 4 heroes and 12 monsters. The minis come complete with the stat cards (so you can use them in skirmish, too). The highlight of that is surely the Black Dragon, which is usually a rare figure and quite coveted.
The whole package has a list price of $25 afaik, so it's cheaper than even a single core rulebook. If you find that you don't like D&D after that, you didn't loose too much. And even if you do like it, you have another set of dice (you cannot have too many dice) and some nice minis.
