5 Books About Relationships In Your 20s You Need To Read

Being in your 20s means college, heartbreak and moving into the real world. Even though there isn’t a magical book that can tell you what to do in every situation, there are books out there to help you along the way. From finding out your sexuality to learning how to play the dating game scene, relationship advice is only one read away.

Check out these 5 best books about dating and relationships in your 20s and see which ones you’d love to read.


Playing With Matches By Hannah Orenstein

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In a world of dating consisting of left and right swipes and cringy Tinder conversations, this book couldn’t be more timely. Sasha Goldberg, a recent journalism grad from NYC finds herself at one of New York’s elite dating services, Bliss. This true story follows Sasha and her career as a matchmaker, but also her own not so great love life.

If you’re looking for some dating app advice from dealing with rejection and how to be the best match, while following Sasha’s own rollercoaster dating scene, check out Playing With Matches.


Things You Should Already Know About Dating You F*cking Idiot By Ben Schwartz & Laura Moses

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You’re on a first date, and things seem to be going well but then all of a sudden your date looks at you like a f*cking idiot, seem familiar? This book was written towards millennials and how to navigate through the dating world as a young adult.

With 100 different dating tips like “stop playing games” or “why are you texting in just emojis, dummy?” Things You Should Already Know About Dating You F*cking Idiot, teach both girls and boys the ins and outs of dating in today’s world.

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When Katie Met Cassidy By Camille Perri

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Katie Daniels, a recently dumped 28-year-old meets Cassidy Price, a sexy and confident New York woman and things begin to change. Katie is faced with questioning her sexuality, and throughout the book, you can see her struggle with what she thought she knew to what she begins exploring.

“When it comes to Cassidy, Katie can’t think straight.” This romantic comedy is about finding out your sexuality and gender identity when you’re in your 20s. For anyone who is struggling to find themselves or in the middle of a sexual identity crisis, When Katie Met Cassidy, is a must-read.


Hey Ladies! By Caroline Moss & Michelle Markowitz

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A fictitious group of eight 20 something and 30 something-year-olds are followed for one year of their life. From vacations to breakups to planning a wedding, this group of women will grow on you and even remind you of your friends and even yourself.

Based on the column of the same name that was on The Toast, anthropology, feminist and hilarious website that shut down in 2016, Hey Ladies! Brings that same light back. The story is also told through emails, text messages, DMs and various other communication methods. If you want a humorous and gossip-filled read, you have to read this book.

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Unwifeable: A Memoir By Mandy Stadtmiller

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A memoir based on failed relationships and nights that ended with one drink too many makes this read just way too relatable. Unwifeable A Memoir goes deep into the world of New York City, surpassing the glitz and glam of what is the surface and really portrays a “Carrie Bradshaw,” and Sex In The City vibe throughout.

Not to mention this book was endorsed by dating columnist for New York Magazine and the New York Post, Cheryl Strayed as well as the Courtney Love, so there must be juicy dating realness with every page turn.


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