17 Books Every Woman Should Read When She's 25

There are certain milestones in life: losing your first tooth, experiencing your first kiss, finding out that life isn’t always fair, and turning 25. The last two kind of go hand-in-hand. Twenty-five is when you’re oh-so young but you feel oh-so old (don’t worry — you’re not). It’s when the term “student loans” morphs from a hopeful thing into your worst nightmare. And it’s when you’re secretly pinning images of people climbing Mt. Kilimanjaro or trekking through Mongolia to your “Things To Do” Pinterest board as you sit inside your cubicle at work.

But it’s not all bad. Twenty-five is when you (hopefully) start along the path of figuring out what you want your life to look like. Or maybe you just want to kick back with your friends at happy hour and philosophize about your last worst date. Either way — books can help.

I’m not talking about super “serious” self-help books that instruct you to pray to the Cosmos and chant over some burning sage in hopes of getting all the answers. I’m talking books full of pain, suffering, one-night stands, outrageous journeys, and hilarious mistakes. Assuming you read some staples like The Bell Jar, Catcher in the Rye, On the Road, and Fear and Loathing in Las Vegas while you were brooding and dreaming in high school and your early 20s, here are 17 books that everyone should read at 25.

They could change your life, or they might just entertain you. Either way, it's a win.

Chocolates For Breakfast by Pamela Moore

Moore’s novel was considered scandalous when it was published in 1956, which is reason enough to check it out. It’s about Courtney Farrell, a teenager who is shuttled between her struggling actress mother’s Hollywood apartment and the boarding school world of her wealthy, detached dad in Manhattan. It’s Gossip Girl meets Catcher in the Rye. It’s perfect if you need a literary heroine who is full of ennui, just like you.

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A Heartbreaking Work of Staggering Genius by Dave Eggers

This funny, tragic memoir struck a chord with twentysomethings everywhere when it was published in 2000, and it launched Eggers’ career. Read it if you want to reconnect and appreciate your parents and siblings.

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Eleanor & Park by Rainbow Rowell

Yes, this is about teenage love, which is why it’s good to read (or reread) at 25. Say everyone on Tinder sucks and you’re not adorably meeting someone in a bookstore the way they do in movies, and you just need a little reminder that true love exists and it can be quietly explosive and subtly mind-blowing. Eleanor & Park (soon to be a film!) will give you hope.

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My Horizontal Life by Chelsea Handler

If, on the other hand, you are meeting lots of people on Tinder or at bookstores and you’re accidentally on purpose waking up next to them in the morning, Handler’s essays about her many, many one-night stands is worth a read. I think it’s her funniest book by far.

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Loose Woman: Poems by Sandra Cisneros

If you finish My Horizontal Life and feel the need for some poems celebrating female sexuality, take a peek at this one. She is a “lust goddess without guilt.” And it just gets better from there.

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Fear of Flying by Erica Jong

This one’s a classic that caused a sensation in the early 1970s (how on earth could a woman be so uninhibited?!) and sold more than 12 million copies. Jong’s story is funny, painful, and relatable. It’s about one woman trying to shake off the shackles of those tired 1950s notions of what a woman’s role is in the world. Basically, she’s just trying to figure it all out, and making mistakes along the way. Like you. Probably.

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Just Kids by Patti Smith

Are you trying to make it as a painter or singer or dancer? Is the notion of the “struggling artist” starting to look a little less romantic to you, because of things like rent and bills and the cost of gasoline? Let legendary punk singer, poet, and artist Smith rekindle your passion and light a fire under your ass. She struggled. She and Robert Mapplethorpe survived by drinking coffee and gnawing on heads of lettuce, and it was all worth it. It’s also just a beautiful, tender, poetic memoir that's well worth your time, no matter how old you are.

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White Teeth by Zadie Smith

Smith and Dave Eggers both burst onto the scene at the same time, and Smith’s debut novel quickly gained an impassioned fan base with its story of the odd-couple friendship between Archie Jones and Samad Iqbal. Read it if you’re feeling the need to celebrate the simple things in life, like your friends, and real human connection regardless of race, class, creed... Just read it.

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The Best of Everything by Rona Jaffe

Any story about female friends trying to make it in the big city will be compared to Sex and the City until the end of time, and that’s OK. It’s not such a terrible touchstone, but it definitely wasn't the first. Jaffe’s 1958 novel about several friends working in publishing and trying to make it in New York is a little dated, but it’s still a fun read.

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Heartburn by Nora Ephron

Every woman should read Nora Ephron, and what better time to start than in your mid-20s. Ephron was a beloved essayist, revered filmmaker, the woman who created Harry and Sally and the “I’ll have what she’s having” scene — and she left us way too soon. Heartburn is her bittersweet (and largely autobiographical) novel about a painful divorce that also manages to be hilarious and uplifting. The movie with Meryl Streep and Jack Nicholson is fab, too.

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Self-Inflicted Wounds by Aisha Tyler

Tyler — comedian, actor, writer, businesswoman, and voice of Lana Kane on Archer — also happens to be a very witty essayist. Self-Inflicted Wounds is all about growing up awkward, making nerdy mistakes, and still coming out OK. Funny and inspiring.

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The Diary of Anaïs Nin by Anaïs Nin

Maybe you dream of escaping your 9 to 5 gig and running off to Paris cafes to contemplate life and fate and the simple beauty of a baguette. It’s time to immerse yourself in Anaïs Nin — lover, philosopher, poet, manic journal-keeper. Don’t be surprised if you find yourself looking up Paris plane fares when you’re halfway through the book, though. Not my fault.

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Tiny Beautiful Things by Cheryl Strayed

You can read Wild, too, but this one is full of advice and insight straight from Strayed’s “Dear Sugar” column, which has just recently been resurrected — hooray. You’ll find bits of wisdom about breakups, bad sex, good sex, jobs, and the meaning of life.

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The Beach by Alex Garland

It’s best to read this at 25, because at 35 or 45 it might not have that same je ne sais quoi. If you’re full of wanderlust, you'll love this book about a hot, sexy backpacker who finds an idyllic, mysterious lagoon in Thailand full of hot, sexy travelers. The movie version with Leonardo DiCaprio is pretty hokey, but he’s also hot and sexy, so there’s no harm in watching it after you finish the book.

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I Was Told There’d Be Cake by Sloane Crosley

Like Aisha Tyler, Crosley finds the humor in being awkward, screwing up, and making colossal mistakes. If you’re in the mood for something a little lighter than Anaïs Nin, these very funny essays are worth a read or two or four.

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Bossypants by Tina Fey

Whether you’re an aspiring comedian/SNL writer/kick-ass Golden Globes host or not, Fey’s memoir is worth a read. It’s funny as hell, obviously, but her stories and insight about working her way up and busting through the boy’s club will probably have you underlining passages as you’re dealing with your own career frustrations, starting with: “You can’t be that kid standing at the top of the waterslide, overthinking it. You have to go down the chute.” Thank you, Tina.

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Slouching Towards Bethlehem by Joan Didion

Now that everyone’s heads have collectively exploded because of those Céline ads featuring Joan Didion, we can all get back to reading her work. She’s a master essayist who wrote: “One of the mixed blessings of being twenty and twenty-one and even twenty-three is the conviction that nothing like this, all evidence to the contrary notwithstanding, has ever happened before.” Wise words.

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So there you go. A bookshelf full of memoirs, novels, and bittersweet essays that'll make that magical year — 25 — just a little bit better.