“I don’t need to read about what should come naturally,” I told my sister, after she insisted I pick up some dating books. I’d been swiping my way through the world of online dating, and my adventures, while always story-worthy, were exhausting. My sister, ever the life guru, suggested I grab some reading material on navigating the down-and-dirty jungle of the online dating world.
Those familiar with the blog know I’m an equal opportunity reader, loving mysteries and chick-lit, literary fiction, medical nonfiction, and everything in between. So why the resistance to dating books? Something in me squirmed at seeking advice about what had once come so naturally.
But it was time to admit there was nothing natural about trying to decide if someone was a potential soulmate or a potential serial killer through four photos and a 250 character bio. I needed to hit the books. Now, perhaps, more than ever.

Marriage was an economic institution in which you were given a partnership for life in terms of children and social status and succession and companionship. But now we want our partner to still give us all these things, but in addition I want you to be my best friend and my trusted confidant and my passionate lover to boot, and we live twice as long. So we come to one person, and we basically are asking them to give us what once an entire village used to provide: Give me belonging, give me identity, give me continuity, but give me transcendence and mystery and awe all in one. Give me comfort, give me edge. Give me novelty, give me familiarity. Give me predictability, give me surprise. And we think it’s a given, and toys and lingerie are going to save us with that. Ideally, though, we’re lucky, and we find our soul mate and enjoy that life-changing mother lode of happiness. But a soul mate is a very hard thing to find.
― Aziz Ansari, Modern Romance
Out of all the dating books I read, Ansari’s is the most grounded and practical. If you are looking for strategies on how to snare a man, then scroll down further, as there are other books for you on this list. But if you are looking for a dating state of the union of sorts, taking inventory of our tech-mad modern dating scene, then Ansari’s book is the one for you. Equally suitable for men and women, and a variety of ages, this is the book to read if you are thinking of dipping a toe into the dating pool. Ansari combines practical advice with research, placing himself in the role of the hilarious, super-smart, straight-shooting dating sidekick you didn’t realize you needed until you read Modern Romance.

I regularly hear women complain about manly-man boyfriends who could stand to be cut down to size every now and then. How can this be done? With the ultimate power move: by using the top four male weaknesses–hair, penis size, career, and height–to keep a man’s ego in line. Any man worth his salt will take this technique in stride, remaining confident enough not to fold while you pick up some relationship power. Women who do this cleverly always come out on top.
– Steve Santagati, The Manual
This book made me laugh. It made me want to cry. Do I mean that in a good way? I have no idea. I wasn’t sure if Steve Santagati was joking when he suggested that I wear little dresses to the hardware store to find a man, but I’ll never know if his suggestions worked as I never tried them out.
Santagati offers a glimpse inside the brain of a true bad boy: himself. He’s a woman-whisperer of sorts, and is willing to offer some of his sweet nothings up for our consumption. This book is half mind-games, half-male fantasies. It’s difficult to take seriously at times, but ultimately harmless and easy to read.

That’s the big picture, your happiness. And health. You should never care what a man thinks of you—until he demonstrates to you that he cares about making you happy. If he isn’t trying to make you happy, then send him back from “whence” he came because winning him over will have no benefit. At the end of the day, happiness, joy…and yes…your emotional stability…those comprise the only measuring stick you really need to have.
― Sherry Argov, Why Men Love Bitches: From Doormat to Dreamgirl – A Woman’s Guide to Holding Her Own in a Relationship
If this book had a theme song, it would be “You Spin Me Round” by Dead or Alive. This is the ultimate mind game book. There are some aspects of Argov’s advice that I love: don’t bend over backward for your man, keep your own life on track, and make sure your happiness is your first priority.
But despite insistence that you should be number one, most of the advice about self-care is centered around the ultimate goal of finding a man. Instead of leading a busy, happy life, Argov seems to be advocating looking busy and acting happy to bait a man on in. It didn’t work for me. If I want to call someone? I call them. I just lay my cards on the table. If you do the same, then you’ll never be able to follow the rules laid out here. But if you need some boundaries in dating and you’re not sure what that looks like, pick this one up.
It’s Not Okay: Turning Heartbreak Into Happily Ever After by Andi Dorfman

Do I think I made a mistake in getting engaged? Yes. Obviously, considering it didn’t last. Do I regret it? Yes. I regret the fact that I will never get that first proposal back; that moment won’t go to my husband, but rather will always belong to my ex. But, I’ve never believed in living life free of regrets, it’s too much pressure. In fact, I regret plenty of things: the terrible bangs I had in third grade, the hideous sequined corset I wore to the prom—hell, I regret what I wore last weekend. Regrets are mistakes that we learn from. They don’t dictate the rest of our lives, they’re just little glitches, and impulsive choices we made in the moment. But it’s just that, a moment and the moment eventually passes.
― Andi Dorfman, It’s Not Okay: Turning Heartbreak into Happily Never After
This is an exposé of the Dorfman affair, aka Andi Dorfman getting engaged to Josh Murray on her season of The Bachelorette, and then it all ending after the show. Mixed in with Dorfman’s story about her season on The Bachelorette and her break-up with Josh is her advice on dating, and more importantly, picking yourself up when a relationship, marriage, or series of 3 Bumble dates that had potential just doesn’t work out for you.
I love books like this, and I’m not afraid to show it. Is it well-written? Nah, not really. Is it urgent advice you’ll hear nowhere else? Nope. Is it juicy gossip about Nick Viall’s sexual prowess, mixed with the comeback story of a woman whose break-up was gossip fodder for the entire nation? Yes and yes. Go there and don’t be ashamed for it.
Women Who Love Too Much by Robin Norwood

We may be hard-pressed to explain to family and friends how someone who is not particularly admirable or even likable can nevertheless arouse in us a thrill of anticipation and an intensity of longing never matched by what we feel for someone nicer or more presentable. It is difficult to articulate that we are enchanted by the dream of calling forth all the positive attributes–the love, caring, attention, integrity, and nobility–we are sure are lying dormant in our lover, waiting to blossom in the warmth of our love.
– Robin Norwood, Women Who Love Too Much
If all of these other books tackle the surface issues of dating: the mating rituals, the call and response preening and courting that finding a good man entail, Women Who Love Too Much goes deeper. It looks at your history, from childhood on, and examines why we date who we date. Why we try to change the people we insist on being with, even when it hasn’t worked out. Why we attach to a certain type of figure, when that type always brings the same sort of heartbreak.
Although not everything in Norwood’s book felt right on for me, Women Who Love Too Much made me realize that dating, for the most part, needed to be an inside job. Most of the dating books, like The Manual or Why Men Love Bitches, that focused on when to call or what to wear, wouldn’t serve me. I needed to tune in to me, and tune out the rest. Then everything would fall into place.
Although I’m usually the book nerdiest, in this genre, I’m totally out of my depth. If none of these dating books sound good to you, this is just the tip of the gigantic dating-book iceberg. I only explored a small handful in what is a huge genre full of all types of books. Gimme some of your faves!






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