Never underestimate the power of the right book. Our relationships with reading books have changed as the world becomes increasingly digital, and we experience near-constant stimulation from the various screens in our lives. Modern technology may have transformed the way and frequency with which we engage with books, but the value of spending time with a book remains unchanged.

dating books award

Books, now more than ever, provide readers with the opportunity for intentional engagement. In a world that seems always to be pushing us to the next and newer thing, taking a moment to fully and consciously engage with the written word is nothing short of precious.

These books offer fresh and thoughtful perspectives for modern daters, whether they’re reentering dating after divorce or navigating the hubbub of dating in their 20s. From personal stories to psychological insights, each book gives daters the chance to engage, digest, and reflect in a special way for the Digital Age.

“First Date Stories” by Jodi Klein

Dating changes for women in midlife, and “First Date Stories” proves the experience can be wonderful, fulfilling, and deeply meaningful, regardless of its results. Author Jodi Klein takes readers through the stories of real women dating in their 40s and beyond, from the lows to the highs and everything in between. Each story offers a different outlook, and Jodi’s reflections help readers understand how the story can guide them to a better dating experience.

first date stories

“First Date Stories” takes the approach that every date holds great potential, regardless of whether it leads to another date or not. Jodi shows her readers that they can learn new things about themselves, other people, and what they’re looking for in romance with each date. Older single women can often feel isolated while dating, and “First Date Stories” provides the empathetic and relatable real-life stories many women need. 

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“Never Chase Men Again” by Bruce Bryans

Never Chase Men Again” teaches women how to get the guy they want and keep him. Bruce Bryans has written numerous books for men and women who are navigating the complexities of relationships and is especially interested in topics related to masculinity, attraction, and gender dynamics. Bruce focuses on giving readers advice they can conveniently implement in their dating lives and then see real results.

never chase men again

“Never Chase Men Again” explores how men appraise potential partners and gives women insider information about what men are looking for. Bruce encourages single women to keep strong boundaries and center their personal values while dating. He also explores how secure and confident relationships begin with secure and confident individuals. 

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“You Only Fall in Love Three Times” by Kate Rose

In “You Only Fall In Love Three Times,” Kate Rose explores the three different types of love and the key to finding a great partner. “You Only Fall In Love Three Times” guides readers to investigate who they are and what they want, using the framework of the three kinds of love Kate identifies. These three kinds of love are The Soulmate, The Karmic Love, and The Twin Flame, and Kate shows readers how each type of love offers and teaches something different.

you only fall in love three times

Kate gives readers a unique language to understand the types of romantic relationships they’ve had in their lives. Kate characterizes The Soulmate as the first love that opens the door to the idea of love but isn’t meant to be for whatever reason. The Karmic Love can be painful, confusing, emotionally turbulent, but ultimately a learning experience. Finally, there is the Twin Flame, the love that helps us accept ourselves, flaws and all.

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“Looking for Something Serious” by Lauren Josephine

If you’re struggling with online dating, “Looking for Something Serious” is the one for you. Lauren Josephine shares her own tumultuous ride through the journey of online dating in a funny and relatable way that nearly any online dater can understand. Lauren explores the ways online dating creates “micro-relationships” and how engaging with one after another can be exhausting.

looking for something serious

Aspects of online dating can be exhausting for singles, especially when they’re not meeting people they want to continue to pursue. Lauren combines straightforward honesty with the kind of humor an online dating veteran will appreciate in “Looking for Something Serious.” The book shows that online dating can be tiring and scary, but it can also be a fulfilling and worthwhile experience.

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“Anxiously Attached” by Jessica Baum, LMHC

Anxiously Attached” is a guide for anyone who wants to become more secure in their relationships. Author Jessica Baum is a Licensed Mental Health Counselor and created “Anxiously Attached” to serve as a guide and resource for people wanting to improve their relationships and form secure connections. Jessica shows readers how to create boundaries, communicate their needs, and understand how their bodies and minds experience anxiety.

anxiously attached

Attachment styles have a profound impact on the way we form relationships. Jessica explores different attachment styles and gives readers the tools they need to understand how they form relationships and why their style of attachment may not be serving them. “Anxiously Attached” urges readers to become secure in their relationship with themselves first before stepping into dating. 

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“Have Him at Hello” by Rachel Greenwald

Rachel Greenwald is a matchmaker, speaker, relationship expert, and the author of “Have Him at Hello.” Rachel collected data from thousands of in-depth interviews with single men over the span of 10 years to try to answer the question of why some dates lead to long-lasting relationships and others don’t even get a call back. “Have Him at Hello” compiles confessions from 1,000 men about what makes them fall in love – or not.

have him at hello

Rachel’s goal for “Have Him at Hello” was to give women insight into how single men approach dating so they can use this information to improve their own dating experience. The book focuses on how to make a great first impression while staying true to yourself, complete with practical first date tips and insightful romance-realted statistics. 

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“The New Truth About Dating” by Laura Charanza

The New Truth About Dating” says what everybody has been thinking: Dating just isn’t what it used to be. Online dating has dramatically transformed the way we meet people and build relationships, and with it, a whole new set of poor dating etiquette has appeared, from catfishing and zombieing to breadcrumbing and ghosting. Online dating can be challenging, but this doesn’t mean it isn’t worth pursuing. 

the new truth about dating

In “The New Truth About Dating,” Life and Recovery Coach Laura Charanza shows readers how to take their online dating experience from a source of heartbreak to a source of happiness. Laura teaches readers how to use technology to their advantage, identify incompatible potential matches, and discover an extraordinary dating experience. 

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“How to Talk to Anyone” by Leil Lowndes

How to Talk to Anyone” offers daters practical and easy-to-implement tips to improve their communication. Leil Lowndes offers nearly 100 tips for anyone who wants to develop the kind of interpersonal skills they need to make friends, land the job, or find a great partner. Leil gives insight into what makes some people great communicators and lets readers in on the habits they keep to create fulfilling conversations and relationships.

how to talk to anyone

Great communication is a learned skill, and even the best communicators among us are lifelong learners. Leil covers small talk and interesting discussion topics, and explores why listening may be the most important aspect of having fulfilling conversations. “How to Talk to Anyone” combines the ideal mix of useful advice and wisdom to help daters develop the conversational confidence they’ve been looking for. 

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“Thank You, More Please” by Lily Womble

Thank You, More Please” by Lily Womble shows single women they don’t have to follow any arbitrary dating “rule” that they don’t resonate with. Many single women are inundated by the same outdated advice and opinions that have been going around for ages, whether it’s related to them being “too picky” while they date or stigmas against unmarried women. Lily takes a feminist and anti-patriarchal approach that flips dating on its head and puts women in the driver’s seat of their own dating experience.

thank you, more please

Lily is a feminist dating coach who has experienced her fair share of toxic situationships. She knows what it feels like to go through the trials of dating and tailors her advice to independent women who feel out of place in a traditional dating scene. “Thank You, More Please” encourages readers to find a joyful dating experience and never settle again.

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“Securely Attached” by Eli Harwood, MA, LPC

Securely Attached” by Eli Harwood, A.K.A. the Attachment Nerd, shows readers how to find increased connection, confidence, and security in all of their relationships. “Securely Attached” is a guided journal that combines two decades of Eli’s clinical insights with tips and resources that make exploring and improving attachment styles straightforward. The book includes 140 prompts that will get you thinking about how you form relationships and what areas may need improvement going forward.

securely attached

“Securely Attached” is a wonderful resource for any person — not just daters — wanting to improve the relationships in their lives. The book is especially pertinent to daters who are healing from past relationships and want to figure out what went wrong. Through reflection and data-driven advice, “Securely Attached” gives daters the tools they need to unlearn negative habits and implement healthier ones.

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Relatable and Empathetic Voices Make Dating Easier

If you’re feeling like you’re in a dating rut, don’t worry. Dating is a journey that can be difficult to navigate at times, and feeling stuck or directionless is part of many singles’ journeys. People tend to have better dating experiences when they have multiple sources of support along their journey. 

Each of these books and authors offers wisdom for daters at any stage, whether they’re making their first dating app profile or trying to rescue a relationship on the rocks. When you feel a little lost in the ups and downs of dating, dig into one of these impactful books, learn something new, and find a dating experience that truly serves you.