walkies: if you want to learn how to play fantasy football, i'd suggest googling "fantasy football 101". it'll point you to several sites with good introductions.
in a nutshell, fantasy football involves choosing which players on your vitual team will "play" for you that week (you have more players than starting spots, so some "play" for you while others sit on the bench). you get fantasy points based on how well the player does in real NFL football. note that you can have players from different NFL teams, you pick who is on your team during the season-starting draft. after that you can add and drop players throughout the season. it's not quite as immediately interactive as D&D - you make choices, then set back and see what happens.
unfortunately it's too late to join the League930, we've already held our draft. but every purveyor of fantasy football services (yahoo sports, espn, cbs sports, sports illustrated, etc) allows you to join a public league (or get some friends together and start a league). consider this year a practice run and join us next year.
You've never played Dungeons & Dragons in your life.
what makes you say that? he's got an over-active imagination, he's into conspiracy theories, he spends a lot of time online... sounds like the modern-day hallmarks of a former D&D'er to me.