Tip: Edith Wharton novels are basically Gossip Girl.
1. The Diary of a Young Girl by Anne Frank
Thanks to the unabridged version, we get passages like Anne describing her vagina: "there are little folds of skin all over the place, you can hardly find it. The little hole underneath is so terribly small that I simply can't imagine how a man can get in there, let alone how a whole baby can get out!" WORD.
But on a serious note: Beautiful and sad writing for all the reasons you learned about in school. I know! Sometimes assigned reading is good.
2. The Bell Jar by Sylvia Plath
Hyped for good reason. Bright, pretty twentysomething New York women's magazine intern in the Mad Men age falls into a deep depression and has a stint in a mental hospital, paid for by an elderly benefactress. Twentysomething angst has been the same since the caveman years.
3. To Kill a Mockingbird by Harper Lee
The moral questions of racism, the nostalgia of childhood, and general social taboos are explored in this Southern Gothic novel. Also, Atticus Finch = Dream husband. Or dream father. Or both. (Messed up, y'all.)
4. Lolita by Vladimir Nabokov
More than just a trendy movie poster that hangs on undergraduate girls' dorm room walls, Nabokov's somewhat-grody classic teaches us the important lesson that even articulate, well-bred and scholarly men can be gross kiddie-touchers.
5. Slouching Towards Bethlehem by Joan Didion
Didion, patron saint of all willowy women with long dark hair and poker faces who write in Moleskine notebooks on the train, authored elegiac essays about Haight-Ashbury in the '70s, leaving New York, the Hollywood scene, and why she keeps a notebook. Excellent for women and also humans of all kinds.
6. Veronica by Mary Gaitskill
A no-longer-beautiful woman, now a decrepit housecleaner, looks back on her time as a teen model in Europe in the '80s, and a close (and uglier) friend who had died. The antithesis of glitzy fashion-industry tell alls. Will make you feel less f*cked-up.
7. Self-Help by Lorrie Moore
Subtly hilarious short stories that are sort of the classier version of Girls. Here, a twenty-two year old woman tells the married man she's sleeping with how she spent her New Year's Eve: "There were three guys, all in purple shirts and paper hats, who kept coming over and asking me to dance. But I danced, and on 'New York City Girl,' that song about how jaded and competent urban women are, I went crazy dancing and my slip dropped to the floor. I tried to pick it up, but finally just hat to step out of it and jam it into my purse. At the stroke of midnight, I cried."
8. Hard To Get: Twentysomething Women and the Paradox of Sexual Freedom by Leslie C. Bell
Bell, a sociologist and psychotherapist who specializes in women's sexuality, spoke to countless twentysomething women about hooking up, relationships, and what they feel they should want versus what they actually want. What she ended up with is probably eerily close to the contradictory feelings you've personally had on the subject, but haven't been able to express.
9. Gone Girl by Gillian Flynn
Not only is this bestseller a wonderful thriller about the most f*cked-up marriage of all time, but it has the now-infamous Cool Girl monologue, whose accuracy and articulation will make you fist-pump into the air victoriously.
10. The Touchstone by Edith Wharton
Short and devastating. One of the lesser-known Wharton novellas, it is about a married man who sells his stash of unrequited love letters — written to him by a homely girl who went on to become a famous author — after the woman's death in order to make a buck. What a dickhead. The takeaway here is to stay away from dudes who might sell your intensely personal shit if you ever get famous and then die.
11. Cherry by Mary Karr
Acclaimed memoirist Karr chronicles her wild teenage years, drug use and sexual awakening in rural Texas in the '60s.
12. Quick Shots of False Hope, Laura Kightlinger
Before Bossypants and Is Everyone Hanging Out Without Me, deadpan actress and comedian Kightlinger, whose face you might recognize, or maybe not (that's what the book is about, really), wrote a sardonic, depressive, honest memoir about living her life on the very edge of fame and fortune and never quite making it.
13. The Secret History by Donna Tartt
At a liberal arts college in the '80s, a normal guy falls in with a brilliant, eccentric group of kids who dress like Tom Wolfe and worship a charismatic Latin teacher. Surprise! Bad stuff (including murder, incest, blackmail, pneumonia, and group sex, if that's considered a bad thing) happens. The takeaway: Stay away from pretentious college students and take Spanish.
14. Delores Claiborne and Gerald's Game by Stephen King
These two King books are considered his feminist departure. The first is about a hard-bitten small-town mom who has just been arrested for killing the wealthy old woman she worked for. The second is about a married woman whose husband just died of a heart attack in the middle of kinky sex — she is left chained to the bed in handcuffs in a remote cabin in the woods, and eventually comes to grips with a traumatic defining moment of her childhood. Both are riveting, disturbing, memorable, and convincing female voices by King. (Delores is also my mom's favorite book/movie, if Carol Breslaw's opinion influences you in any way.)
15. A Good Man Is Hard to Find by Flannery O'Connor
Contains the famous observation that people would all be good "if it had been somebody there to shoot [them] every minute of [their lives]."
16. My Ántonia by Willa Cather
The last book in Cather's prarie trilogy, about women's rights but disguised as a love story.
17. Little Women by Louisa May Alcott
While Little Women suffers a bit from Sex and The City Syndrome (everyone thinks they're Jo/Carrie, nobody wants to be Beth, Meg, Amy/Miranda, Samantha, Charlotte), it is still worth reading, especially for Laurie (a.k.a. Christian Bale in the movie): "Someday you'll find a man, a good man, and you'll love him, and marry him, and live and die for him. And I'll be hanged if I stand by and watch."
18. The Robber Bride by Margaret Atwood
A gender-flipped version of the folktale of the Robber Bridegroom, featuring three women with nothing in common except the manipulative, potentially-dark-magic-wielding Zenia, who came close to ruining all of their lives. Actually, everything by Margaret Atwood.
19. Jane Eyre by Charlotte Brontë
Even though a dude who hides his schizophrenic first wife in a wall isn't exactly an ideal romantic hero. (Are you married? Did you check behind all your walls?)
20. He's Just Not That Into You by Greg Behrendt
No, it's not a classic. Yes, it is kind of trashy. But, as someone who has read all of the books above, I will tell you that the lesson it contains can be just as important.Specifically, it can free you up from some guy you're chasing and give you plenty of time to read all of these books.
