In Anna David’s new memoir, Falling for Me, the author sets out to find the empowering side of being single by following the advice set forth in Helen Gurley Brown’s groundbreaking 1962 book Sex and the Single Girl. So should we be living more like women in the ’60s? We talked to David (whose book launch we’re sponsoring in New York City Oct. 10) about that — and why it’s still so hard to be single.

You recently ignited a bit of a blogger controversy by asserting in a post that “women had it better in the ’60s.” Do you really think women had it better then, hands down? Or just in certain ways?

Definitely just in certain ways. Which is what I said in the piece! But I get that when people want to pick a fight with you — or are, say, angered simply by the title of your piece — they don’t see words that might minimize their vitriol. My point was that I wish women would stop making statements about things that don’t matter. I love Gloria Steinem and am incredibly grateful for all that she’s done, but for her to go around making a stink about the Playboy Club TV show when everyone knew the show was terrible and wasn’t going to make any kind of cultural impact seems silly. Instead, I’d rather she talk about things that do matter and we can change, like how judgmental and cruel women can be to one another simply because we always see each other as competition.

How do you think the perception of single girls has changed over time? Or has it?

Well, contemporary society certainly didn’t invent the notion of a spinster or the idea of a single woman being lonely, damaged, or desperate. But when there were fewer opportunities for women, I think it was probably much easier to concentrate on finding and working on a good marriage. Yet our generation was told — or at least I was — that we had to have incredibly successful careers as well as successful marriages. And I know very few women who manage that but hundreds of men. Of course, we now also have millions of shows, blog posts, Op-Eds, Tumblr groups and what have you out there to perpetuate the idea that we should be able to have it all or that single women are pathetic. We put these cultural messages out there; I mean, if you think about The Real Housewives of New York, Bethenny was repeatedly called the “underdog” when she was single. Then she landed a husband and she’s the show’s great success story, off to her own series!

But I don’t really know why we have such a hard time making singlehood okay; maybe it’s threatening to a still patriarchal society that needs procreation in order to survive. Maybe it’s that no matter what we do, some women are always going to find fault with others for their choices.

How do you think we can change the way single women are perceived?

I think we can all work on being open to one another’s choices. And look, I’m as much a part of the problem as anyone because I judge the shit out of women who are perfectly capable of working but instead rely on their husbands entirely — especially when they try to make a big show out of their “work” when really it’s some dilettante-ish thing their husband is funding. And the truth is I judge them because I’m jealous, on a certain level. A part of me wants to have a man say, “Honey, don’t worry about the money. How about you try making that scrapbooking business idea a reality? You’ll have my full support.” Yet ever since I’ve become aware of the fact that my judgment is based on jealousy, I’ve been trying to curb it — by reminding myself that I don’t know what these women’s lives are like, that I don’t know what they’ve traded or had to swallow and that maybe it’s a lot more challenging than anything I do. And with awareness, couldn’t we all — even the Smug Marrieds — stop congratulating ourselves so much and in turn finding fault with the way other women are living?

Is it a failing of the feminist movement that we haven’t been able to move past this?

Yes, in a way I do see this as a failure of the feminist movement because it’s something we can change and we don’t need men to help us. And it’s about spreading positivity rather than negativity. I mean, I get that anger is often required in order to make a difference, but when certain women make the same arguments over and over again about how there aren’t enough women allowed in one field or another, I just don’t know how effective it is. Most people subconsciously tune out those who sound angry because they assume the people aren’t being rational — that’s a psychological fact. And sometimes those arguments fall into that category. Of course, what I’m talking about isn’t something you write an Op Ed or create a Tumblr group about and then hope men change but actual humble efforts of self-examination and trying to change ourselves, which is arguably the most challenging thing in the world.

What was the most important thing you learned from the journey you took in this book?

It was that I had to stop defining my life based on what the world seemed to think it should be. I love my parents but I was definitely raised by people who have very specific ideas about How Things Are Done and love was sort of doled out based on how “successful” you were. I spent years trying to please them and not succeeding and then very much took that attitude into the world; I was going to succeed at this life game if it was the last thing I did. But in growing up like that and then continuing to be that way, I’d neglected to really ever ask myself what did I want? What made mehappy? And really hitting an emotional bottom and then deciding to devote my life to the principles of a book from the ’60s forced me to get to a place where I could really start to question what I’d always valued and to build a life that involved more than just creating a bright, shiny career. Maybe it would have happened anyway — maybe this is just the place I’m at in my life — but I came to realize I could change those things I didn’t like and learn to really love what I did.

Can we ever balance our seemingly innate yearning for love with, well, all the other things we have to do in our lives — careers, friendships, and the general pursuit of fabulousness that seems to be required of modern womanhood?

It’s definitely possible. I think it takes a certain emotional maturity that I’m only now beginning to feel like I possess. But we have to make sacrifices and give up certain fantasies. The fact is, I know only two married women with incredibly successful careers and in both cases, the husband essentially agreed to remain entirely subordinate — to either give up his career entirely or to just do it more as a hobby. I think a lot of Type A women want a Type A man but most of the Type A men seem to want yes-women. This idea a lot of women have about having it all — the big life, the great career, the successful husband, the group of friends, the fabulousness — is, I think, a fantasy. And somehow doing my book taught me that that’s okay, that it’s not about doing or having it all but being happy with what you have.

What’s the biggest problem with the way we approach sex today versus the Sex and the Single Girl days?

I think we’re as confused about sexual mores as we’ve ever been. Back in Helen’s day, girls either slept around or didn’t and most didn’t. But we were raised at a post-women’s revolution time, where we were told that liberated women could do whatever they wanted. And yet we were raised by women who’d come of age during Helen’s time so that message, to me anyway, always came out contorted or conflicted. Just because we have the Pill and the freedom to do whatever we want sexually, that doesn’t mean we’re always going to feel great about it. I’ve felt ashamed or like I did too much or like I shouldn’t have done something after many sexual experiences and I think many women feel an intrinsic level of shame when they have sex outside of a committed relationship. The fact is, sex is still, on some level, something women give and men take and we act like it’s not — like we’re liberated and everyone’s in the same boat. We’re not. And in many ways I think it was healthier when female sexuality was regarded as more of a gift — when it wasn’t so easily accessible. Until the day that a man could be called a slut and it would be viewed as something other than a compliment — a day I don’t really foresee coming — I believe the way we view and approach sex will be screwed up. I also think that while sex is everywhere — porn stars like Jenna Jameson and Sacha Grey have broken out into the mainstream, Kardashian-wear is sweeping the nation — our society is still so repressed. We’ll worship these sort of déclassé examples of female sexuality but won’t have open, honest communication about sex. And then everyone’s so shocked when wealthy golf players and politicians are embroiled in sex scandals. I actually have one section of my book that’s sexually very graphic and a few months ago, I panicked: called my editor and asked if we could take those six pages out. It was too late as it turned out, but my sudden shame wasn’t about me — I’d written the pages, after all, not to mention had the experiences I documented — but about how other people would judge me. And I think that if we as a society were as open and honest about sex as I wish we were, I wouldn’t have been so scared of that.