10 Must Read Books For Single Girls Who Want To Start Dating Again


December 22nd, 2018   |   Updated on June 29th, 2022

Being single is fun but after a point of time, it becomes a tad boring. As soon as you decide that you are willing to get into the groove once again the problem arises that your mind is still confused.

Mostly it wants some more time to actually settle down while your heart is raring to go. Books in such situations can be extremely helpful and guide you in different ways possible.

But then the million dollar question is which books to read. Not your run of the mill ones here is 10 must-read books for single girls who want to start dating again.

These books have been chosen very carefully and are going to help you take the first steps to take a plunge once again.

Not only that some of them are going to be your help when you meet someone interesting but are not sure whether he is the right one or not. Grab these to know how you can bring a spark in your love life.

1. Never Have I Ever

Never Have I Ever

If you’ve ever struggled with dating (or, at the very least, had plenty of mishaps of your own), Heaney’s laugh-out-loud book might just be the one for you.

As a twenty-something who has never fallen in love or had a real boyfriend, she writes about unrequited crushes, the (very real) struggle of connecting with potential partners, and the pervasive feeling of being the lone wolf when all your friends seem to be paired off.

If you’re worried about entering the dating field as a new player, this is a great read to keep your spirits high, even if things aren’t always looking so great.

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Review: Jan C.

Fantastic!! Never stopped smiling throughout the entire READ. The author has a sense of humor that is darn near identical to mine. I see myself in pretty much every scenario an it’s fantastic! Sometimes, it’s just what you need for someone else to tell you about your own life and listen to their advice. I am confident that whatever is supposed to happen will happen in my life, but for now it’s always a good reminder to live each day to the fullest. Enjoy where you are now, don’t kill yourself thinking about the place you want to be someday; chill, all in good time. Thanks Katie!!


2. It Ended Badly

 It Ended Badly


You think your last breakup was bad? Think again. The title of this book says it all: author Jennifer Wright took a good, hard look at our world’s history and pinpointed the 13 worst breakups of all time. This is definitely a good read if you’re struggling to put your past behind you or grappling with guilt over your actions, because Wright is able to put your own bad breakup into perspective and remind you that in the grand scheme of things, it was just one little bump in the road that is your entire life.

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Review: Deborah

This was a great, gossipy romp through history. Some reviewers (who, no doubt believe that history is supposed to be boring and that to make light of it borders on sacrilege) have complained about Wright’s cavalier style, but I found it charming. What I really like about Wright, however, is her soft heart and keen sense of morality and compassion. She treats her subject matter tenderly, as if she is always aware of how painful love can be. I get the sense that she is constantly thinking of the heartbroken who may be reading her words and she wants them to be comforted and reassured.


3. What We Not Finna Do

What We Not Finna Do

Erin McLaughlin’s dating manifesto is short, but it gets the point across: in ten points, she makes it clear that a lot of us deserve a lot more than we’re willing to stand for, and she wants to change the game for women everywhere. McLaughlin opens up about her own struggles in past relationships and deconstructs social constructs that oftentimes plague (primarily heterosexual) relationships. McLaughlin is funny, insightful, and smart, and if you walk away from this read with anything, it’ll be an idea of what to do in your next relationship — and what you really, really shouldn’t do.

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Review: Liza Bolanos

This is an amazing book that skips all of the therapeutic concepts and replaces it with real talk. Better than 99% of dating self-help books out there. This book does a great job of deconstructing social discourses negatively impacting hetero relationships and offers new ways of being. As a therapist/instructor who utilizes social constructionism/feminist theory and wrestled with these ideas on the regular, I will most definitely be recommending this book!


4. A Sucky Love Story

A Sucky Love Story

Honestly, sometimes love just sucks. YouTuber Brittani Louise Taylor learned this the hard way, which she shares in her debut memoir. When she met Milos, a hot Serbian doctor who was studying in San Diego, she had a weird feeling about him, though she couldn’t put her finger on it.

But after a whirlwind love story that included an engagement, a pregnancy, and maybe even a threat or two from a possible Serbian mafia leader, Brittani slowly began to realize that the man she fell head over heels for wasn’t what he seemed.

Her story of love, loss, and survival is both mind-blowing and eye-opening and is a definitely must-read if you’re thinking about jumping back into modern dating anytime soon. After all, while Brittani’s not-so-love story might sound a little crazy, it could easily happen to anyone.

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Review: Robyn Ousby

I can’t remember when Brittani’s videos showed up in my recommended on youtube. I guess it was the video where she announced that she had a boyfriend she met at a coffee shop. I watched, even when I found her puns annoying. She was genuinely a nice person. After reading this book it should show everyone, you have no clue what celebrities or online personalities are living. They show what they want.


5. Bridget Jones’s Diary

Bridget Jones's Diary

The truth is that there are probably a lot more fiction that deals with meeting and falling in love with your perfect match than fiction that deals with the woes of dating. Bridget Jones’s Diary has a little of both.

The titular protagonist is a single thirty-something woman who enjoys the life of the uncommitted one minute and frets about dying alone the next, all the while trying to improve her life one day (and one gym visit) at a time.

If you’re a single woman who’s struggling to reach your goals and meet the man of your dreams, or even if you just want a good laugh, the hilarious Bridget Jones might just be the one for you.

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Review: Kindle Customer

Helen Fielding is an excellent comedic in this Bridget series. The first portion of the book Bridget had me laughing right at the start. Her New Years resolution was long with will not and wills. But there were some resolutions that I could even relate to.

The English slang words were both cute and funny. There’s also Jone’s abbreviations that even I found myself using for a little while.


6. The Ethical Slut, Third Edition

The Ethical Slut, Third Edition

Let’s be honest here: modern relationships don’t all look the same. What works for one couple might not work for another, and what works for your friends might not necessarily work for you.

If you’re interested in something more nontraditional, The Ethical Slut is a great guide that’s all about “love, sex, and intimacy beyond the limits of conventional monogamy.”

The book covers (but is not limited to) polyamory, open relationships, asexuality, and cross-orientation relationships. It’s the perfect place to start if you’re wanting to dive into a nontraditional dating style but aren’t sure how to begin.

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Review: It’s Just Me

A lot of good advice can be obtained from this book. The writing style is very “preachy” in my opinion, so you may want to take things with a grain of salt and keep an open mind. I’ve also heard it referred to as “hippy-ish” writing, which I think matches as well. Definitely worth a read though if you’re looking to understand yourself and others around you.


7. Is Everyone Hanging Out Without Me?

Is Everyone Hanging Out Without Me?

Mindy Kaling is, in many ways, a modern-day model for what it means to be the fun, single girl who’s had her fair share of ups and downs in the dating world. You can see it reflected in her most popular works, from The Office (where she played the hilarious Kelly Kapoor, who had an on-again-off-again relationship with her co-worker, played by her real-life on-again-off-again beau B.J. Novak) to The Mindy Project (where she played a rom com-loving, financially independent but boy crazy gynecologist who takes New York City’s dating scene by storm).

It turns out, these personas aren’t too far off from who Kaling really is, making her a hilarious, familiar narrator as she shares her insights about life, love, and all things Hollywood. If you’re looking for dating advice from an old friend, this is the closest thing you can get in book form.

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Review: TheBookishHobo

Is Everyone Hanging Out Without Me? was such a joy to read. I devoured this book in two sittings. And it wasn’t just one long joke either. There was some real substance to her writing. A lot of legitimately laugh out loud funny moments, but other more deeper moments too. With the turn of each page, you see Mindy grow and mature. Her writing is raw and honest. You feel like you’re sitting down with Mindy over a cup of coffee and something sweet (although, of course, not a cupcake; she doesn’t eat those anymore).

I think every woman at any age could find something to relate to within these pages. And I think that’s a real testament to not only the quality of the writing, but also as to the quality of the author herself. The book wasn’t perfect and there were a few moments that were a little slower than others, but she still deserved five stars. It was evident she poured out all of herself into this book. And that’s something you don’t always get. Mindy you have a life-long fan in me!


8. Tiny Beautiful Things

 Tiny Beautiful Things

Sometimes the best way to keep yourself centered while dipping your toe into the modern dating scene is to sit down with a good book of advice, and Tiny Beautiful Things is just the one. Cheryl Strayed wrote for The Rumpus‘s advice column, Dear Sugar, for two years, and this book is a collection of her most popular pieces. You know what that means: there’s going to be a lot of insights, a lot of self-reflection, and a lot of hit-you-in-the-heart moments. Dating can take a lot out of you — sometimes you just need to focus on the tiny beautiful things.

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Review: Jayne

A marvelous book, Tiny Beautiful Things reminded me of the prevalence of human suffering and the part we can play in easing one another’s burdens. Based on an advice column, Dear Sugar, it’s filled with letters to Sugar asking for advice on love, heartache, disappointment, and suffering. From cancer to adultery and death to Christmas, Sugar responds with tough, shrewd compassion. She doesn’t candy coat her responses or pull any punches. And yet…and yet, no one who reads them could dispute her genuine concern and compassion for her advice seekers. She calls them “sweet pea,” and signs her letters, “Yours, Sugar.”


9. The Love Gap

 The Love Gap

In some ways, dating is a game, and it’s good to know the rules before you start playing it. Luckily, Jenna Birch knows exactly what to do, and she has tons of research to back it up. Birch dissects why smart, successful women who are succeeding in work seem to be failing in love and manages to pin down some of those annoying dating patterns you’ve noticed with men over the past few years, including ghosting and an unwillingness to commit. If you want to take a step into the dating field feeling confident and aware of how men think — and why they act the way they do. TC mark

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Review: C. Sun

I was in a relationship with a Mr. All That But the Bag Of Chips. He was, on paper, “all that.” Our weekly dates were episodes of The Bachelor: private jets, operas, surprise shopping sprees with Swarovski-studded shoes, in addition to conversations about philosophy and goals and dreams and the future of humanity, sprinkled with daily I-Love-You’s. But something was missing.


10. Spinster


If you’re thinking about dating but aren’t so sure you’re ready for the time commitment and the sheer amount of energy, both emotional and physical, that goes into it, you might want to give this book a look before you make the decision. Kate Bolick makes a compelling argument about why more and more women are choosing to remain single and looks into the lives of women in history who have proven that sometimes the best thing you can be is your own damn savior.

Even if you’re dead-set on dating, this is a pretty great read if you want to feel empowered and emboldened to ensure that you’ll never settle for less than you deserve — because if being in a relationship doesn’t make you happier than what you could be while single, why bother?

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Review: Happy Camper

Now, as far as to whether this book actually delivered? I’d have to give it 3 stars (and that is a bit generous). I found her point somewhat elusive. I’d be reading and thinking, “Yeah, yeah . . . okay, I get it,” and a paragraph later or at the end of the page I’d have lost the thread. Or maybe I didn’t lose the thread– maybe I was looking for something more subtle or something more significant and it’s not there. Maybe the point the point of the book really IS as simple as it seems: that marriage has historically been the focal point of women’s lives to the detriment of their individual development. Well, huh.


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