Dating is fun, but I also think we can all agree that at times, it can be straight up exhausting. With new dating apps cropping up every month and gender expectations changing all the time, dating is somehow both easier and harder than ever before.
Whether you’ve been single and on a dating hiatus or you’ve just got out of a long-term relationship, it can be daunting to jump back in and start playing the field again. But have no fear — if you’ve got a concern, we’ve got a book for that. Check out our favorite reads about dating, from self-help books to tell-all memoirs that cover the woes and wonders of dating in the modern age.
A Sucky Love Story: Overcoming Unhappily Ever After by Brittani Louise Taylor
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.
Never Have I Ever: My Life (So Far) Without A Date by Katie Heaney
I read Katie Heaney’s memoir in college, and boy, did it resonate with me. 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. But don’t let that description fool you — Katie is anything but sad and lonely. Instead, she is funny and insightful and, best of all, knows exactly how to have a good time as a single woman in a society that’s constantly telling her that love is the one thing worth dying for. 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.
What We Not Finna Do by Erin McLaughlin
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.
It Ended Badly: 13 Of The Worst Breakups In History by Jennifer Wright
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. The book description truly says it all: “It Ended Badly is for anyone who’s ever loved and lost and maybe sent one too many ill-considered late-night emails to their ex, reminding us that no matter how badly we’ve behaved, no one is as bad as Henry VIII.”
Bridget Jones’s Diary by Helen Fielding
We’ve got a lot of memoirs and essay books in this list, but what about fiction? 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.
Tiny Beautiful Things: Advice on Love and Life from Dear Sugar by Cheryl Strayed
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.
The Ethical Slut by Janet W. Hardy and Dossie Easton
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.
Is Everyone Hanging Out Without Me? (And Other Concerns) by Mindy Kaling
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.
Spinster: Making A Life Of One’s Own by Kate Bolick
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?
The Love Gap: A Radical Plan to Win in Life and Love by Jenna Birch
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.