From the bedroom to the boardroom, the past 60 years have seen many a win for women. The pill gave us control over our own reproduction in 1960, and in 1973 Roe v. Wade did more of the same. Women have broken ground in politics, business, literature and art, giving new voice to female desires. There have also been back steps and sidesteps, missteps and mistakes. For a closer look at the modern female, we tracked down a dozen influential women, from artists to intellectuals, to discuss what we've gained and lost. Some spoke in their homes over glasses of petite sirah and boxes of Chinese takeout; others in Manhattan cafés over bowls of oatmeal. All helped provide a frank and honest look at the current state of our sexual lives.
There is almost no positive place for a woman to stand and be sexual, on a sexual journey, in our culture.—Naomi Wolf
Men are having their 39th birthday parties at Disneyland. these are the men we're supposed to be pro-creating with?—Natasha Leggero
Writer, advertising consultant, founder of MakeLoveNotPorn.com
The older I get, the hornier I get. People ask me why I date younger men, and it's very straightforward: I like having sex. I like having a lot of sex. I'm all about lots of stamina and short recovery periods, which men my own age, sadly, are not going to deliver. And in a context in which I'm focused on my work and my ventures, I'm not looking for a relationship. I don't feel I'm necessarily a relationship person, to be perfectly frank. I don't think I'm a monogamous person.
Every time I say publicly that I date younger men, I feel I'm striking a blow for all womankind. But I'm also public about it not because I'm saying I think everyone should do what I do, but because to me it's a matter of a much bigger point, which is that I believe everyone should be free to decide the relationship model that works for them. Which may, by the way, be different at different points in your life.
I'm very open about the fact that I date younger men casually and recreationally. I date a lot of them; I keep the pipeline refreshed constantly. But I have one key criterion: They have to be very nice people. I have a good radar for very nice people. As a result, I date only utterly lovely young men, and I date them in an atmosphere of mutual trust, respect, affection and liking. Some of my so-called casual relationships go on longer than most people's committed ones.
The great thing about older woman–younger man is that I can have all the chiseled cheekbones, bulging biceps and six-pack abs I want. And I enjoy all that, obviously. But at the same time, I'm just looking for what I find attractive about this person. They don't have to be conventionally good-looking; they may be quirky, they may be interesting. I might really love their forearms. It drives a completely different assessment, which is much truer, to just see a person for who they are and see how you respond to that. In 11 or 12 years of online dating, I have never had a bad first date; my filtering sensors are very, very good. I've met men I did not feel attracted to and ended it. But I've never had a bad first date. One of the most paralyzing dynamics, in life and in business, is fear of what other people will think. And we absolutely apply that in a dating context as well. There is an external-facing dimension to how we assess our dates—and I don't have any of that. I would love people to think differently about how they look at whom they date, in a similar way.
Stand-up comic, actress
One guy I work with, I won't say his name, he's on television and he makes a lot of money. He was making fun of me for having an assistant. I said, "Well, I just want someone to go to Rite Aid and the post office. Who picks up your dry cleaning and buys the dog food?" He was like, "I have a wife." And I was like, "Yeah, I'd like a wife too." And he said, "Well, she doesn't work. She's in charge of running the household and raising the family." And then he goes, "Sometimes I'll walk down the hallway and throw something on the floor, just so she knows the division of labor."
Men are keeping tabs. It is kind of a fucked situation that we're in, because all women are working. We have aspirations, and we don't have time to pick up full-time after a man. I do have a lot of thoughts about this. I think it would be nice if women could have wives. I was trying to think lately of someone who has everything. Like, if there are any female stand-up comedians who have a touring schedule, an acting career and a family. There really isn't one. There was Phyllis Diller. She had those things. She had a TV show, a family and a stand-up tour. There are a lot of men like that. There aren't really any female touring comedians who have children, whereas there are tons of males, because they all have wives. It does make it hard for women to have everything.
Now more than ever, the thinking woman and the career-driven woman and the woman with ambition, she has to find a partner. Now women need someone who's only going to help and add to their lives. If that's not going to happen, they break up. I have friends in their 30s who are freaking out about having a baby. Meanwhile, men who are in their 30s are barely ready for pet ownership. They're having their 39th birthday parties at Disneyland. These are the men we're supposed to be procreating with?
Editor of xoJane.com, founder of Sassy and Jane magazines
I remember with Sassy we were the first magazine to give teenage girls information on birth control and STD prevention, and we also wrote about gay teenagers, which was considered so controversial at the time that we lost our 15 biggest advertisers. Then we were taken off about half the newsstands we had been on. It seems like things have moved in a pretty progressive direction in terms of giving that kind of information to young women. In the just over two years that xoJane has been around, we've done 187 articles on abortion. That shows how much we are still fighting the abortion-rights battle, that it would still be such a big topic. Whereas, some of those other things—obviously gay rights are still a huge issue, but we've come such a long way.
To me, there are always new frontiers. One of the things I feel I am addressing a lot more these days is issues of gender, gender as a fluid concept. It's becoming more and more a part of the way I produce the website and the media that I produce for women. Even to the point that, when I talk about xoJane being a website for women 18 to 34 or 18 to 49, it feels really old-fashioned to me to say it's for women. What makes it for women, as opposed to just for people? I don't know if people identify themselves in that way as much as they used to. In terms of the way we write and talk about sex with women, a lot of times you could read the article without gender pronouns and not know whether it was for a man or a woman because it's so much about getting what you want sexually and what works for you.
Now it's more acceptable to be open about just wanting to hook up or be casual and not want a relationship. I never wanted to get married, was never interested in it. Recently I've found that more women just love being single and don't have any interest in that either. I think it is important for women to hear from other women that it is an option. It is an option to not be monogamous with one person for the rest of your life. There are huge industries built around being married and coupling off. It's the same with women who don't want kids. There's not really a voice out there. For me, as someone who didn't want to get married, I almost felt as though I was missing some chip or gene or something that makes women see a bride and then want to be a bride.
Author of more than 20 books, including Fear of Flying and Seducing the Demon
What is fascinating to me is that there's a nutty minority that wants to take back all the rights of women. A woman who can't control her own fertility can't control anything about her life. It's the bedrock of women's freedom. These guys who are passing crazy laws about sticking sonogram wands up women's vaginas know the laws will be overturned. They're taking a stand for the benefit of the fringe minority that votes in midterm elections. The majority doesn't agree with them, so what we're seeing is democracy being perverted for the sake of a well-organized fringe. It's interesting to watch, and distressing. If you go back in time, Hitler didn't have a majority when he came to Munich. He did not have a majority, but a very well-organized minority can come to power in a democracy. Watching it happen is truly amazing.
One thing you can see is that fascists always want to keep women barefoot and pregnant. And what is it about? It's about fear of women, fear of women's immense physical power—the power to give birth—and if they can't stop it, they want to control it. Women are mysterious objects. Women control the means of reproduction, and it's necessary to keep them in the power of men.
It's so irrational and crazy, because every UN report on the status of women has shown that wherever you educate women, wherever you give women birth control, the whole society goes up economically in just a few generations. But if you keep women from education and from birth control, the whole society becomes impoverished. So what they're basically doing is something that's good for no one. It's such a primal desire and so completely illogical. It's interesting to me that here we are, nearly 100 years after the women's vote, going through this again. It's just mind-boggling.
Author of four books, including Prozac Nation; lawyer
In love, there is no equality. I'm a hardcore feminist, so if I am saying that, it must be true. Living with a man means picking up his dirty socks and bringing him coffee and pastries in bed, and it means he always comes, even if you don't. The reason it is crucial that women make a lot of money and have a lot of power in the public sphere is that it is not going to happen in private, if they love men. I know this. I drive a hard bargain as a writer and a lawyer. David Boies is one of the most powerful men in the world, and he will tell you that I don't work for him—he works for me. But when it comes to love and the men I love, I am a slave. It is a pleasure to serve: I love being in love. That's just the way it is.
The book I'm writing now is going to be called YES: A History of Love at First Sight in New York City. I am sorry for all the times I said no. And I don't mean to sex. I'm happy for all the times I said no to sex, because it was probably not nearly enough times. But I'm sorry for all the things I said no to, like the times people said, "Come with me to the movies," and I was like, "No, I'm tired." I'm sorry for all the times I was tired and just didn't do something. I'm sorry for all the times I was cranky, because I should have gone out. I missed a movie; I missed going to a very good museum exhibit. I'm sorry for everything I said no to. I'm sorry for trips I said no to, because as you get older, fewer things come up. They just do. Life becomes more boring in general. And it's too bad. You should just do everything you can do. I'm sorry for all the things I haven't done; I should have done everything. I should have done all the things that were a dumb idea, that would have compromised my dignity—which is not so important. That would have been, you know, just fun. But mostly I can't complain, because I said yes to most things. I am not somebody who spent a lot of time avoiding things. And I think that's better.
I've always considered myself to be a very sexual person. I had sexy thoughts when I was little. When I was three years old I had a recurring dream about a witch who would put me in an oven and cook me, and then she would take me out and eat me. I was like, "Oh yeah! Cook me! Cook me, witch! Put me in that fucking oven and cook me. Do it, do it." That was my first sexual thing, and I don't know what that means. I was always interested in sex.
I had a lot of boyfriends and a lot of flings. I think flings are great. That's something women should investigate a little more thoroughly. The trick is, you have to not care. I was in my late 30s when I first started having successful flings and didn't get emotionally attached to the guy. But you have to be at a point in your life when you're not needy, when you're not looking for a husband or a long-term boyfriend or anything.
I feel one of the last taboos is for women not to have children. I'm not going to say I never wanted to have children, but I never had a burning desire to have children. When I met my husband and we got serious and were going to get married, I tried. I was 44, and it was a little bit late in the day. But he was the first guy I was going to try with. I just didn't have that burning desire. If you don't have it, you should honor that. Having children isn't something you should do just because everybody else is. To be in the slim minority of women who don't can be a little unsettling and make you feel like, Well, is there something wrong with me? But I never felt that. My life has been about trying to entertain people. In my own paltry way, trying to entertain people is my service. My service is not raising a family. I know you can do both, but that just wasn't my thing.
The other taboo is a new taboo: I have not had any plastic surgery or any injections or anything done to my face or body. And that is the new taboo. People are mortified. People look at my neck and are like, "Oh God, what is that?" I think it's great and fine for other people, and there's certainly a lot of new technology out there that's not as invasive. You can end up getting stuff done and look reasonably okay, but it's not for me. I just want to see what's going to happen. Also, somebody's got to play the old lady in the movies, and sooner or later I'm going to be the only one who doesn't look like she's 40. And I'll be working.
Author of eight books, including The Beauty Myth and Vagina: A New Biography
There is almost no positive place for a girl—a teenage girl, a young woman, a woman—to stand and be sexual, on a sexual journey, in our culture. There was this brief, shining moment when I was growing up in the mid-1970s that really influenced me. I grew up in the Haight-Ashbury in San Francisco, and it was like anything was acceptable; you were weird if you weren't at least bisexual. Being gay was a revolutionary, positive thing. Everyone was open and exploring, including women. And also the culture for a moment was not yet so pornografized—probably because of technology. When men and women encountered each other, they were learning about each other from each other, rather than from this giant for-profit industry of pornography.
One thing that's being documented is how quickly sex becomes boring if you masturbate to pornography and so you need to ramp it up to what one young man who talked to me about his porn addiction called "the kink spiral." I keep seeing this in pop culture: the choking thing, angry anal, aggression. It's not that I'm passing moral judgment, but it worries me as a human being that porn makes us so desensitized to sex itself—which is supposed to be this revolutionary, transformational power—that we need to ramp it up with aggression.
My objection is not to pictures of naked women. What has happened to Generation Y and teenagers is that everybody grows up already addicted to online porn. What worries me is that porn doesn't liberate sex; it closes it down.
I haven't seen Playboy lately, so I don't know how explicit it is, but I could see a movement that encourages teenage boys to subscribe to a magazine that has naked, pretty women sitting there, rather than turning on a video. It's almost romantic compared with what's online. How nice. Women are beautiful. I'm going to get all kinds of shit from feminists for having said that.
Adult-film star, owner of Burning Angel Entertainment
Porn stars are more touchable now. They're not on pedestals like they used to be. People know a lot about them thanks to social media. So much of their information is out there and easy to access; it's a little different from the image of the porn star in the early 1990s. It's like that with musicians too. If they have a mental breakdown, everyone knows about it. It doesn't really matter, because you have to adapt with the times no matter what. In some ways it's better and in some ways worse.
For me, most of the changes are probably a good thing because I'm not an untouchable-looking blonde Barbie doll. If my entire persona were based on my being perfect-looking, then I probably wouldn't have a career in porn. I've definitely been able to thrive off of cashing in on the way I look and also my personality—that's how I've been able to connect with fans. I probably wouldn't have been able to be who I am had I done porn in a different decade.
I can't speak for anyone's career but my own: I have never been subjected to anything bad just for being a woman. I know some people may have that image of porn. I'm not saying porn is the right place for every woman in the world. A career where everyone is looking at you, where you're out there to be judged, can be very tough if you don't have a thick skin. I've never felt degraded. I never let being a woman get in the way of anything I ever do.
Author, sex educator, adult-film director
I think we've finally seen the emergence of smart and quite purposeful porn stars. The narrative was either you were plucked off the bus from the Midwest and coerced into doing porn, or you somehow fell into it and now you're there. But then people like Jenna Jameson and Sasha Grey, and to some extent Belladonna and Stoya, began to emerge—these are women who are 100 percent in control of their jobs, their branding, their marketing, their businesses. That really is a shift. And then they, of course, become role models for the next generation. "Oh look, we can do this with standards and boundaries and still possibly move on to something else." They became role models.
On a superficial level, I definitely like the changing aesthetics of who qualifies as a porn performer. There was a time when there was a dominant aesthetic, when if you wanted to make money, you had to have this kind of California-girl look: blonde with blue eyes, surgically enhanced boobs, a tan. The truth is, that's one standard of beauty, but there are also tattooed and pierced girls, punk rock girls, girls with pink hair, girls who aren't a size two, girls who are flat-chested, girls who have an indistinguishable ethnicity. All these different tropes have come in, featuring women with different bodies, different aesthetics. Many of them have managed to achieve success; that has opened the playing field for who can be a performer, who can be a porn star. The people who dominate the female performer pool are white and thin. So there's that. We aren't there yet. But we are in a better and different place from where we were. Hopefully that's going to keep moving. Some of this parallels mainstream Hollywood in many ways. It's not just the porn industry.
Filmmaker, author, artist
Just two days ago I was doing an event and a woman asked me, "How come there is so much sex in your books and everything you do?" Part of me was grateful she noticed, because no matter how far in that direction I go, people tend to still just call me cute.
Unless you're being overtly erotically sexual as a female, people almost don't clock it as sex. What I said to her was that the territory feels so wide open to me; it feels, surprisingly at this point, that still not much has been done with sex. We're seeing the same things done again and again, so it just feels fun, like it's not hard to think of something no one has ever done. And that's not true with most things that are so much a part of life. A lot of smart people have walked all over everything else. And also, it's an intersection of power and intimacy and shame and vulnerability, and boringness, potentially—all these things that are interesting to me. It's not even necessarily that sex is so interesting; it's that you can get at all these interesting things through it. That has evolved, I think, initially coming out of being a child. I was focused on the sexuality of children, which is pretty impossible to do anything about.
With my first feature film, Me and You and Everyone We Know, I was thinking there should be, that that should exist as its own thing, separate from what we think of as real sex, like adult sex. Children have their own ideas of that, and in some ways that's part of children's right to have their version of sex, whatever that is in their heads. I remember thinking this is such a debatable idea, it needs its own sort of branding and logo. I was consciously thinking that when I came up with the "back and forth, forever" symbol, ))<>((, that we used in the movie. I was thinking it could be like the Coca-Cola or Nike logo but for children's sexuality. So it can have humor in it, because it is funny. It gets less funny as you get older. Kids can see what's funny about all that. I think that has its own power. And it did kind of work. I think managing to brand children's sexuality is pretty radical and could even be potentially threatening in a way. Especially a woman doing that—because I'm supposed to be maternal, or I'm just so caught up in my own orgasm.
Dr. Ruth Westheimer
Sex therapist, author
Certainly more women know that they have to take responsibility for their sexual satisfaction. Even if their partner loves them, he cannot know what they need to be sexually satisfied. We know that today—not just because of me; there are other people in the field of sex education—there is a tremendous increase in women who know what they need to be sexually satisfied. Women have learned to be the initiators, to not wait for sex to be initiated, to know that this is important for them and their partners. It's not that she's going to be aggressive. She is going to be assertive and knows how to be sexually literate.
Also, I think Playboy was very important. Hugh Hefner knows me, but not in the biblical sense of the word. Put that down! Not knowing in the biblical sense, but I certainly have met him many times. I'm grateful to him, because the foundation of free speech certainly had a tremendous influence on issues of sexuality—on talking about it, on being able to discuss it. I want to say one thing for Playboy: I have always told mothers that if they find Playboy under their boy's mattress, never talk about it. Make believe you never saw it and leave it there.
Comedian, actress, television host, author
I think people have an unrealistic expectation of marriage. I think they have an unrealistic expectation of their spouses. I think most people don't know what they're getting into, and they're more excited about the wedding than they are about the marriage. A lot of people are just not cut out for it. Marriage is not for pussies. It requires an infinite amount of patience, not just with the other person but with yourself. And it requires a willingness to allow someone else to be flawed, and their willingness to allow you to be flawed as well. What makes a great marriage is finding someone who is willing to see the best in you at all times. That doesn't mean they are a Pollyanna or blind; it just means they see what in you is equivalent to greatness.
I am probably not your typical woman. My husband and I play Xbox together, I love video games, I engineer my own podcast, I love computers and I'm an early adopter. I own probably seven devices. So for me, technology has been great. You know, I probably should spend more time having sex and less time looking at people have sex on the internet, but I think that's probably everybody's case nowadays. We all have our problems.
I hope men realize now that that picture of their penis is never not going to be on the internet. When society has crumbled and humans have vanished from the earth, cockroaches are going to walk in on iOS 972 and this picture is still going to be on the internet. So just don't do it! Unless you want your great-grandchildren to see your cock, don't do it. It's not going to work out well for you.
Now people are realizing even if you post something and delete it immediately, it's too late. As soon as you press tweet, that is the last time you will ever have control of that image. And I think guys should realize that, for better or for worse, our half of the species is not particularly interested in seeing a picture of your penis anyway. Unless it's a medical marvel and you should be in a museum or a circus, we're not interested. Take a picture of your bank account or your car or your IQ. Or maybe send away to 23andMe and send us a picture of your genetic makeup that shows you don't have any cancer precursors and will never have a heart attack. Send us information we can use. A picture of your dick is not going to get it done.
This article originally appeared in the January/February issue of Playboy. Read more from our complete archives on iPlayboy.com.
Photo courtesy of If We Ran the World/Abosch, Getty, Newscom