I Read Books: About Dating

I’m starting a new feature here- “I Read Books.” I have a tendency to read, close together, groups of books that have something in common, so I’m starting this to share my reviews of what I read, grouped into categories.


As a chronic singleton who’s been actively dating for about seven years, I sometimes look to other people’s experiences for advice. Since it’s Valentine’s Day month, I’m kicking this series off with books about dating and relationships. Actually, I’m pretty sure I read most of these around this time last year.


Never Have I Ever: My Life (So Far) Without a Date by Katie Heaney



I don’t know if everyone would love this book, but I sure did. I am another Katie H. who has always been single and I could relate to so much of what she writes about here- liking guys who like other girls, crushing from afar but not doing anything about it, not realizing when guys are trying to flirt with you. Even though she’s a few years younger than me, her pop culture reference points, as she takes us through her life from elementary school until her twenties, resonated- I laughed out loud on the T when she discussed the incredibly flawed premise of the game Dream Phone and there’s a fantastic chapter about awful online dating messages. But even though she hasn’t found a boyfriend yet, this book is very light, happy, and optimistic. And before the end of the book I realized that Katie kind of has found the love of her life- her best friend and roommate, Rylee. Not in a romantic sense, more like Billy Mack realizing at the end of Love Actually that he people he loves is, in fact, the manager who’s always with him. Rylee, who always has a boyfriend, is a constant source of support and friendship, and as someone whose friendships have sustained her and kept her from complete loneliness, I get how valuable that is.


It’s Not You: 27 (Wrong) Reasons You’re Single by Sara Eckel


This book actually does a really good job giving hope to single people, and that’s not easy. The author was single for a long time before meeting her husband in her late thirties and based on her own experiences and those of her friends and other women who remained single until later than average, she goes through all the reasons women are told they can’t find love and tells you why you shouldn’t listen to them. She actually makes sense. Think about it—it’s not because you’re too independent or too picky or have low self-esteem. You’re single because you haven’t met the right person yet—period.

She throws in some Buddhist teachings to back up a lot of it, and it’s a bit distracting, but this was a quick and comforting read. Seriously, every single woman should read this.


The Unhooked Generation: The Truth about Why We’re Still Single by Jillian Straus

I actually read this book a few years ago, but last year I bought it and re-read it. Jillian interviewed a bunch of urban, single, heterosexual people she identifies as “Gen X-ers” (so it’s a teeny bit dated, but it’s all relevant for millennials as well) and found a bunch of patterns that have contributed to people remaining unmarried longer: unrealistic expectations, unwillingness to work to make the relationship better, “multiple choice culture” that prioritizes keeping options open, fear of divorce, etc. There are a ton of anecdotes from the people she interviewed as well as Jillian herself, but just when you start to get depressed and wonder how you’ll ever meet anyone, she includes a chapter on couples who did make it work and explains why. And now she has personal experience to back it up—turns out Jillian met her husband while she was researching this book.

The tips she gives at the end make sense. They’re not the easiest to follow—“burn your checklist”? My checklist is a mile long!—but they’re based on what works, and often what doesn’t work is couples expecting perfection without putting forth the effort to make the relationship better.

Speaking of checklists…


Data: A Love Story by Amy Webb

Amy Webb certainly had one. And not just things like being a non-smoker or wanting kids—things like which specific musicals she wanted her future husband to like. After a bad breakup, she decided to try online dating, and after a bunch of the terrible dates that most online daters are accustomed to, she decided to get very specific about what she was looking for, eventually coming up with seventy-two criteria. She narrowed those down to the most important, assigned point values to each trait, and used those to determine whom to go out with. She also analyzed the algorithms of the site she was using to determine how to get better matches, partly by creating some fake male profiles to see which women they were shown. Eventually, she met the man who became her husband.

I don’t know if the tricks Amy used would work for everyone, but there are still some good ideas in here—include “girl” in your username, show some skin in your profile picture, don’t mention too much about work because most people don’t like to think about work, etc. And it’s definitely worth considering that fewer dates with guys you’re more enthusiastic about is better than a larger number of bad dates. Aside from that, though, this is just enjoyable to read as a memoir. The writing has a funny, laid-back tone and there was a lot I could relate to— I’ve been doing online dating for seven years and it’s been among the most miserable experiences of my life.

Skin in the Game: Unleashing Your Inner Entrepreneur to Find Love by Neely Steinberg

In November of 2013, I went to a particularly demoralizing Match.com Stir event at a bar. Neely was there promoting her dating coach business, and…let’s just say the night ended with me in tears, sobbing to her about how frustrating my dating life was. She was very nice, and when her book came out, I bought it. It’s all about using the same skills that an entrepreneur uses to work on finding a romantic partner. While the book is a bit longer than necessary and could have benefited from more editing, it does make a lot of good points—after all, you’re not going to meet anyone if you just sit around waiting.


He’s Just Not That Into You by Greg Behrendt and Liz Tuccillo

Ten years old at this point but still relevant. I bought this book back in college, left it on the coffee table, and went out. While I was out, my roommates picked it up and read it, and when I came home, I was greeted with, “Oh, my God, men are ASSHOLES!” We then all had a spirited discussion of the book they’d all flipped through while I was gone.

The thing is, harsh as it may sound, it saves you time and heartache to realize before things get too serious that a guy just isn’t that into you. It frees you to move on and look for love elsewhere. I don’t agree with everything in it—if he’s not asking you out, it might be that he’s just not that into you, but some men are genuinely shy or afraid of rejection—but most of it is genuinely helpful. Why waste time with a guy who doesn’t think you deserve his time?


The interesting thing about these books is that their advice is all different and sometimes different books conflict with each other, but I did find things to take away from all of them. What dating books have you guys read? Any particularly helpful/unhelpful ones?

3 thoughts on “I Read Books: About Dating

  1. Christa

    I’m actually curious to see that Dataclysm by Christian Rudder isn’t on your list. I’d take a gander at that book if you’ve already read (and enjoyed) Data: A Love Story. Dataclysm was actually written by one of the founders of OkCupid who (through a flurry of questionably gathered OkCupid experiments– curse you terms of service!!!) compiles data from OkCupid and churns them into a book, giving readers a glimpse of online dating and the current dating climate. If you’re into stats, etc, or have tried the online dating thing and feel like you’re in a rut– it’s something you might be interested in reading.

    And at the risk of sounding like a self-help BS guru-reader (I normally shy away from those types of books,) the one “self-help dating guru” I actually stand by is Matthew Hussey. His book, Get the Guy, is actually pretty helpful and full of practical advice that applies to pretty much anything in life (not just dating.) Ironically though, I didn’t use much of his advice while using OkCupid (mostly went off my personal experiences and my terrible dating adventures) but realised that a lot of it has stuck because I think of relationships as a choice, and both my significant other and I chose each other. It’s strange, kind of preachy, but a quick and easy read and helps you at least feel like you’re getting out there.

    Otherwise, I love your picks and despite the fact that I’m attached, I’ll have to take a gander at a couple. :)

    1. Katie Post author

      Thanks for the suggestions! None of these books were ones I specifically sought out- I just heard about them one place or another and decided to read them. I’ll give the books you mentioned a try!


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