5. Liz Phair - Exile In Guyville

By now hopefully she's closed her Env2 and is ready to talk about some music. The first album you should discuss is a classic by Liz Phair, her debut "Exile in Guyville". This album is arguably the most female-empowering album of the 90's. It tells tales of growing up, wanting a boyfriend, wanting something less-than-a-boyfriend, and getting over your something less-than-your-boyfriend totally dumping you, even though your relationship was ambiguous in the first place. It is an album that anyone who has graduated from high school can relate to, as she experience feelings that weigh more than any common sense. The album features bedroom songwriting that every girl wishes she wrote. Many critics have also deemed this album as "Women's Studies 101", as Phair accurately and very openly depicts feelings of female adolescence for us ignorant men to study over. Liz Phair paints herself as a rose with a thorn in this album, and by bringing up this album, you will appear as a guy who loves to rock and roll, but is also sensitive and understand's the hipster girl's struggles.