Well i started in high school with the advanced fighting fantasy books with a few friends on the stairs at lunch time (god we were geeks) but we quickly moved onto Warhammer fantasy role-play, which kinda got me and my friends hooked as it was a similar genre to the books and movies we loved such as david gemmell and conan.
So that kinda forms my recommendation i would pick a genre that you and your friends are familiar with and go with one of the bigger games in that field eg
If your are into World of darkness type stuff such as buffy, angel, dresden files then i would go for either the white wolf stuff or the D20 modern system.
If your group are into swords and sorcery i would go for classics such as D&D, runequest or Warhammer or pendragon for knights of the round table stuff.
If Sci-fi is your bag then my recommendation would be cyberpunk.
The reason i have went for the bigger games rather than the indie ones is that these all have a great wealth of background info and i feel are easier to pick up and play for the new gamer, or at least so i found when i started.
However i would recommend a rather quirky game my friend designed called "Best Friends"
http://boxninja.com/ which is "a role-playing game about girlfriends and all their petty hatreds" to quote him. Might be what you are looking for as it is a great concept for any group male or female.