Advice Sexuality

Get Real! I Think He’ll Dump Me If I Don’t Have Sex with Him. So, Should I?

Heather Corinna

Do you want to be with someone who would only stay with you because you're having the sex they want to have?

Published in partnership with Scarleteen

i.ate.the.cookie. asks:

I’m 13 and my boyfriend is 16. I’m a virgin but he isn’t and I feel like if I don’t have sex with him he is going to break up with me. Should we just have oral? Also, how can you tell if someone has already had sex?

Heather Corinna replies:

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The only sound way we can tell if someone has or hasn’t already had any kind of sex is by asking them and accepting their answer.

Obviously, sometimes some kinds of sex can result in certain outcomes, like pregnancy or sexually transmitted infections, which can also tell us if someone has engaged in some kind of sex. But really, even then, the only sound way of knowing is by asking someone and taking their word on it. People won’t always be honest about that, but the idea some people have that how someone’s body parts look or feel can give us that information is just plain wrong. Bodies can’t tell us who has or hasn’t engaged in sex, only people can. I’m more concerned with your first question than that one, though.

What do you want and feel ready for right now when it comes to an intimate, sexual relationship, if you even want one? Does this situation look like that? I’m guessing it doesn’t, since it’s pretty safe to say that no one really wants a sexual relationship where sex is happening only because they feel scared that if it isn’t they’ll get dumped.

Intimate and/or sexual relationships involve being vulnerable, emotionally and physically. That’s not really a choice, it’s part of the deal. How vulnerable we are depends on a lot of things, but we’re always even more vulnerable when we have less agency—when by virtue of the way the world is or our relationships are we’ve got less power or ability to do things than someone else, due to our sex or gender, age, color, how much money we have, how our bodies are, our sexual orientation, and so on. As a 13-year-old girl or very young woman in the world, one with a male partner older than she is, and who it sounds like feels she gets to call less of the shots in her relationship than her partner, I’d say you’re very vulnerable here, and that’s something really important to know and accept.

Because of being vulnerable like that, and especially if you don’t want to take big risks in either of those departments or be more likely to deal with rough outcomes, healthy sexual relationships usually require trust and feeling and being respected, safe, and secure, including emotionally, with ourselves and our partners and having the ability, either on our own or with help, to take care of our physical and emotional health around sex. Those relationships being healthy and beneficial also includes everyone in them feeling as free, as able to say no, maybe, or not now to sex as they do to say yes, being supported in that, and not feeling like sex is something they have to give or exchange for something else, like a commitment or someone liking you only because you did what they wanted sexually. Healthy personal interactions of any kind also require that everyone in them feel valued and respected—like a person, not an object or just as a means to something one person wants. All those things are also usually what everyone in them really wants.

Do you want to be with someone who would only stay with you because you’re having the sex they want to have? Really?

I’m not you, so we might feel differently. But for myself, I know that unless the only thing I want from my relationships is sex, that is not usually the kind of person I want to be with. Heck, even in relationships that are only or mostly about sex, I tend to find that kind of setup is a recipe for crappy experiences since sex that isn’t masturbation, but something more than one person is sharing and a part of, needs to be about what both people want, and leave a lot of room for everyone involved not wanting the same things, or the same things at the same time. Even in sex-only relationships, the kind of situation you think you’ve got here usually spells “BLECK.” If what you want is commitment, then what you offer is commitment. If the other person wants it too, they’ll offer it back. If they don’t, trying to give them something else to get that commitment usually doesn’t work and also tends to leave a person feeling pretty gross and create relationships that are quite lousy.

I can’t tell you what kind of sex to have with this person or not, especially without having any idea at all what kind of sex you want, on your own terms, if any. The only thing I know you want from your post is that you don’t want your boyfriend to break up with you. So, it doesn’t sound to me like sex of any kind is even something you want. When it is, someone usually will say something about that.

If you don’t really want a sexual relationship right now, in general or with this person, what kind of relationship do you want? Whatever that is, that’s what you want to aim for, and make choices that are in alignment with that. But if you don’t really want a sexual relationship with someone, or this guy, right now, and are only thinking about doing it to keep him around, know that that choice isn’t likely to get you what you want.

Sexual choices are very personal, and when we’re going to start making them, while we can get some advice, ultimately we need to figure out what we really want and don’t, what we do and don’t feel ready for, what we are or are not up to dealing with (or what we do or don’t want to deal with), and more, and then all of that for anyone else involved too. Even being ready for that constant and often complex decision-making process takes us some time, let alone making those choices.

Should you choose to be sexual with anyone and want it to be something you feel good about before, during, and afterwards, which supports healthy relationships most likely to make you happy and support your self-esteem, having any kind of sex to try and keep someone around does not make that likely. In fact, it makes the opposite very likely: that you won’t feel good about it at all, and that it probably won’t be something good for you in the short or long term.

What’s more, you should know that one thing we know from statistics and people’s personal anecdotes is that it also doesn’t usually work in the first place. In other words, even if you do have sex with this person to keep them around, or keep them only having sex with you, chances are good that they’ll ditch you in short order anyway if the only reason they were sticking around was for sex.

Now, I don’t know if you’re getting the idea he’ll leave based on his words or actions or if this is more about your own head. If it’s coming from him, then we can know this isn’t a healthy situation. In healthy relationships, people don’t threaten to leave unless someone has sex with them. For sure, sometimes one person wants things the other doesn’t or isn’t ready for, but when that’s the case, there aren’t threats or ultimatums or pressure. In healthy interactions, when people are really different in that way, and the person who wants something feels they can’t deal without it, they don’t seek out relationships with people who aren’t feeling similar, or who they suspect aren’t there yet with sex.

While we’re on the age difference, when someone older—even by just a few years, especially in our teens or childhood where a few years is a bigger difference then it will be later on—is in a relationship with someone younger, one thing they need to be able to do is keep in mind that the younger person is likely to be in a different place than they are. If what they want is “past” where the younger person really is, they need to be able to stick with the younger person’s pace and not try and push, pressure, or nudge them up to theirs. That’s just basic courtesy, but it’s also the biggest thing that supports a romantic or sexual relationship being healthy when there’s an age or development difference (or any big difference in agency). That also tends to take a good deal of maturity, self-awareness, and patience. The fact that a lot of people in their teens and 20s are still just developing those things in a big way is why same-age teen sexual relationships tend to be healthier than those where there’s an age difference of a few years or more.

But these worries might not be coming from him or anything he’s said or done. Sometimes worries like this can come from your own head, or messages you might get from friends, television, or magazines. If we get the message or the idea that sex is either the only thing of value we have to offer, or the thing of the most value, it can be pretty easy to think it’s something we have to do to keep people around who might be interested in sex with us. But the thing is, that’s just not true. Not with people who see our value as more than just that, anyway.

No one who sees and appreciates you as a whole person is going to see your value as only sexual, including you! If and when that’s what someone wants, they get to choose that, but that is very rarely what anyone really wants in an ongoing relationship, especially love relationships. And if you want a boyfriend or anyone else to see you as more than that, you have to do your part, too, which includes being more than just that, and refusing to be only that.

Either way—or maybe if the pressure is even coming from both you and him—I’d say that so long as you’re feeling like sex is something you need to do to so he doesn’t break up with you, you’re not in a space where choosing to have any kind of sex is probably a sound choice. Only if and when you aren’t feeling that way, and sex is something you really feel ready for and want on your own, and when you’re in a relationship or situation where you feel like you can say no and the world will not end, will you be in the right spot to even consider sex as a good choice, and will it be at all likely to be something you feel good about, which is really the point. Sex is supposed to be about feeling good, remember, not just physically, but emotionally too.

Still on the fence? If so, I can toss some more things out for you to think about and talk about with your boyfriend, but also hopefully with other supportive people in your life too.

I think the best approach to figuring this out for yourself might be to ask yourself some questions and ask your boyfriend some questions too. I think if you can come to clear answers to these, you can probably figure out your own best choices here, choices that support what you really want, that don’t involve you doing anything you don’t really want to do and feel ready for, and that also help keep you from exchanging sex for commitment.

Questions for yourself:

  • What do you really want from an intimate relationship with someone right now? If it was only up to you, would you want it to be sexual? If so, what kind or kinds of sex do you really feel ready to engage in and handle? What kind or kinds of sex, if any, do you actually feel comfortable with and truly excited to explore right now?
  • Do you feel pressured to have any kind of sex? If so, where is that pressure coming from—from where or who—and what is that pressure about? What could you do to ditch or shut down that pressure so any sexual choice you make is one made without feeling pressure to make any one choice?
  • How ready do you feel to manage sex with someone else, including the more complicated parts, like saying what doesn’t feel good, rather than just what does, talking about your body parts intimately, having someone see your body, talking with partner and others, like a doctor or parent, about your physical safety (safer sex, contraception, etc.) and your emotional safety (consent and some of the scary or tough feelings sex can bring up)? Right now, with this person, does all of that feel pretty comfortable, and like things you expect will go well and leave you feeling cared for? Is this someone you think can handle these kinds of things himself? How about you? What if he said what you were doing didn’t feel good or wasn’t what he liked, or he told you he had a sexually transmitted infection (STI); could you deal with that right now?
  • Compare two possible ways what you are worried about will happen: where first, you don’t have the sex this person wants and they ditch you, and then where you do have the sex this person wants and they still ditch you. While that outcome may not happen in either case, if it did happen, is there one of those scenarios you think you’d feel better or worse about?
  • How ready does he seem for sex with someone else? One thing we can easily miss or make not-so-smart assumptions about when a partner or potential partner is older is that since they’re older, have had sex before, or they put sex on the table, they must be ready. But age or previous sexual experience doesn’t mean, for example, that someone has learned to be a good sexual partner, that they’re taking care of their sexual health, know how and when to use safer sex (and have been responsible in that way before), can communicate about sex, or can handle it if one or both of you winds up having problems with sex, from the big stuff like an unplanned pregnancy or infection to things like one or both of you just finding you don’t feel good or aren’t satisfied?

In terms of that last one, for yourself and both of you, I’d start by taking a look at this: Ready or Not? The Scarleteen Sex Readiness Checklist.

I’d then look at this: Sorting Maybe from Can’t-Be: Reality Checking Partnered Sex Wants & Ideals.

Take some real time going through those and thinking about them—days, at least, not just minutes or hours. How do you feel about those realities and issues? What do you think about him, specifically, and all of that? This is also something to talk about together. When we’ve heard back from people who took the time to go over this checklist with their partners, they’ve always reported back that they think doing it helped them make their best sexual choices, and when that choice has been to have any kind of sex, they’ve expressed that having the checklist pretty well covered is something they think had a lot to do with sexual experiences they felt great about.

Questions to ask your boyfriend and talk about together:

  • What kind of relationship is he looking for with you? Something mostly sexual, or something bigger than that? Does what he wants really fit with what you want? Does what you want really fit with what he wants?
  • Does he understand that sex isn’t something to “get,” but something to share, and for it to be the right thing for both of you, you need to be as ready for it as he might feel? Is he able to recognize that if you really, truly do not want to have any kind of sex yet, aren’t ready, or only would have sex to keep him around, that having sex with you would be seriously not OK?
  • Is he committed to making sure you don’t feel any pressure at all from him to do anything sexual you don’t want to do for yourself, not just only or mostly to keep him around?
  • What does he see sex as doing for your relationship, and for him and you separately? How about you? Does what each of you expect and want out of sex seem to fit together or not?
  • Is he just as concerned about you not sticking with him? Is your relationship continuing as deeply important to him as it sounds like it is to you? If not, why? Why does he think he feels more secure in this relationship, or less attached to it, than you do?

I know those are big questions and conversations that might make you feel uncomfortable having with him, but this is big stuff you’re considering, after all. And if you don’t feel able to talk about all of this this candidly, or even bring this stuff up with him, I’d say you have your answer right there. If we can’t talk about what we’re thinking about doing and all it entails, then usually, making the choice to do whatever that is isn’t our best choice. When sex feels like something we’re really ready for, that’s right in a given relationship or interaction, even when talking about it is awkward, it’ll be something we can do and know the other person would want us to do. If talking about it and issues around it feel terrifying, we can know that doing it is probably a pretty bad idea.

All of what I’ve said here might also feel really overwhelming. Making sexual choices is complicated, and it can feel like a lot to think about for anyone, at any age, especially outside an ongoing sexual relationship we’ve been in for a long time. But when sex is the right thing for us, even if all we need to consider or discuss is still a little dizzying, it still feels manageable. When it’s not the right thing for us, all we have to think about usually freaks us out, big time.

One more thing to know is that our earliest romantic relationships are most often going to be brief, not go on for a lifetime, years, or even months. When we are really into them, they don’t tend to feel that way—they instead can feel like the way we feel right now is so giant, it’ll last forever. But how we feel is how we feel, and what usually tends to happen doesn’t often follow those feelings in the ways we think it will. And that’s OK. Our earliest relationships, however uncomfortable it is to think about, are supposed to be how we start to learn about what we want and don’t, about how to have those kinds of relationships, not how we finish. Whether you have sex with this person or not, the chances that this relationship will go on for more than a few months, a couple years at max, is very, very unlikely. I’m saying all of that not to be a jerk, but because I want to make sure that you know that no matter what you choose when it comes to sex with this person, they or you are probably going to move on from one another sooner rather than later, no matter what.

Last, it can be really hard to make sound sexual choices without good support and perspective, especially when we’re new to making those choices. I’m really glad that you came here to ask me these questions, but I’d also encourage you to find another trusted adult in your life, someone who knows you very well, who you know cares for you and respects you, to talk about this with. Someone who can tell you how awesome you are, how much more you have to offer someone than a blow job, how lucky anyone is to date you at all, whether you have sex with them or not, and how much you’re already giving someone else by sticking with them, and you’ll know they’re not just saying all that because they really know you and have already cared for you for a very long time, without you having to do anything big for them that wasn’t also right for you and just as valuable to you.

I hope all of this helps you to make whatever choice you strongly feel is best for you and feel really, really good about.

Culture & Conversation Media

Filmmaker Tracy Droz Tragos Centers Abortion Stories in New Documentary

Renee Bracey Sherman

The film arrives at a time when personal stories are center stage in the national conversation about abortion, including in the most recent Supreme Court decision, and rightly so. The people who actually have and provide abortions should be driving the narrative, not misinformation and political rhetoric.

This piece is published in collaboration with Echoing Ida, a Forward Together project.

A new film by producer and director Tracy Droz Tragos, Abortion: Stories Women Tell, profiles several Missouri residents who are forced to drive across the Mississippi River into Illinois for abortion care.

The 93-minute film features interviews with over 20 women who have had or are having abortions, most of whom are Missouri residents traveling to the Hope Clinic in Granite City, Illinois, which is located about 15 minutes from downtown St. Louis.

Like Mississippi, North Dakota, South Dakota, and Wyoming, Missouri has only one abortion clinic in the entire state.

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The women share their experiences, painting a more nuanced picture that shows why one in three women of reproductive age often seek abortion care in the United States.

The film arrives at a time when personal stories are center stage in the national conversation about abortion, including in the most recent U.S. Supreme Court decision, and rightly so. The people who actually have and provide abortions should be driving the narrative, not misinformation and political rhetoric. But while I commend recent efforts by filmmakers like Droz Tragos and others to center abortion stories in their projects, these creators still have far to go when it comes to presenting a truly diverse cadre of storytellers if they really want to shift the conversation around abortion and break down reproductive stigma.

In the wake of Texas’ omnibus anti-abortion law, which was at the heart of the Whole Woman’s Health v. Hellerstedt Supreme Court case, Droz Tragos, a Missouri native, said in a press statement she felt compelled to document how her home state has been eroding access to reproductive health care. In total, Droz Tragos interviewed 81 people with a spectrum of experiences to show viewers a fuller picture of the barriersincluding legislation and stigmathat affect people seeking abortion care.

Similar to HBO documentaries about abortion that have come before it—including 12th & Delaware and Abortion: Desperate ChoicesAbortion: Stories Women Tell involves short interviews with women who are having and have had abortions, conversations with the staff of the Hope Clinic about why they do the work they do, interviews with local anti-choice organizers, and footage of anti-choice protesters shouting at patients, along with beautiful shots of the Midwest landscape and the Mississippi River as patients make road trips to appointments. There are scenes of clinic escorts holding their ground as anti-choice protesters yell Bible passages and obscenities at them. One older clinic escort carries a copy of Living in the Crosshairs as a protester follows her to her car, shouting. The escort later shares her abortion story.

One of the main storytellers, Amie, is a white 30-year-old divorced mother of two living in Boonville, Missouri. She travels over 100 miles each way to the Hope Clinic, and the film chronicles her experience in getting an abortion and follow-up care. Almost two-thirds of people seeking abortions, like Amie, are already a parent. Amie says that the economic challenges of raising her other children make continuing the pregnancy nearly impossible. She describes being physically unable to carry a baby and work her 70 to 90 hours a week. Like many of the storytellers in the film, Amie talks about the internalized stigma she’s feeling, the lack of support she has from loved ones, and the fear of family members finding out. She’s resilient and determined; a powerful voice.

The film also follows Kathy, an anti-choice activist from Bloomfield, Missouri, who says she was “almost aborted,” and that she found her calling in the anti-choice movement when she noticed “Anne” in the middle of the name “Planned Parenthood.” Anne is Kathy’s middle name.

“OK Lord, are you telling me that I need to get in the middle of this?” she recalls thinking.

The filmmakers interview the staff of the Hope Clinic, including Dr. Erin King, a pregnant abortion provider who moved from Chicago to Granite City to provide care and who deals with the all-too-common protesting of her home and workplace. They speak to Barb, a talkative nurse who had an abortion 40 years earlier because her nursing school wouldn’t have let her finish her degree while she was pregnant. And Chi Chi, a security guard at the Hope Clinic who is shown talking back to the protesters judging patients as they walk into the clinic, also shares her abortion story later in the film. These stories remind us that people who have abortions are on the frontlines of this work, fighting to defend access to care.

To address the full spectrum of pregnancy experiences, the film also features the stories of a few who, for various reasons, placed their children for adoption or continued to parent. While the filmmakers interview Alexis, a pregnant Black high school student whose mother died when she was 8 years old, classmates can be heard in the distance tormenting her, asking if she’s on the MTV reality show 16 and Pregnant. She’s visibly distraught and crying, illustrating the “damned if you do, damned if you don’t” conundrum women of color experiencing unintended pregnancy often face.

Te’Aundra, another young Black woman, shares her story of becoming pregnant just as she received a college basketball scholarship. She was forced to turn down the scholarship and sought an adoption, but the adoption agency refused to help her since the child’s father wouldn’t agree to it. She says she would have had an abortion if she could start over again.

While anti-choice rhetoric has conflated adoption as the automatic abortion alternative, research has shown that most seeking adoption are personally debating between adoption and parenting. This is illustrated in Janet’s story, a woman with a drug addiction who was raising one child with her partner, but wasn’t able to raise a second, so she sought an adoption. These stories are examples of the many societal systems failing those who choose adoption or students raising families, in addition to those fighting barriers to abortion access.

At times, the film feels repetitive and disjointed, but the stories are powerful. The range of experiences and reasons for having an abortion (or seeking adoption) bring to life the data points too often ignored by politicians and the media: everything from economic instability and fetal health, to domestic violence and desire to finish an education. The majority of abortion stories featured were shared by those who already had children. Their stories had a recurring theme of loneliness and lack of support from their loved ones and friends at a time when they needed it. Research has shown that 66 percent of people who have abortions tend to only tell 1.24 people about their experience, leaving them keeping a secret for fear of judgment and shame.

While many cite financial issues when paying for abortions or as the reason for not continuing the pregnancy, the film doesn’t go in depth about how the patients come to pay for their abortions—which is something my employer, the National Network for Abortion Funds (NNAF), directly addresses—or the systemic issues that created their financial situations.

However, it brings to light the hypocrisy of our nation, where the invisible hand of our society’s lack of respect for pregnant people and working parents can force people to make pregnancy decisions based on economic situations rather than a desire to be pregnant or parent.

“I’m not just doing this for me” is a common phrase when citing having an abortion for existing or future children.

Overall, the film is moving simply because abortion stories are moving, especially for audiences who don’t have the opportunity to have someone share their abortion story with them personally. I have been sharing my abortion story for five years and hearing someone share their story with me always feels like a gift. I heard parts of my own story in those shared; however, I felt underrepresented in this film that took place partly in my home state of Illinois. While people of color are present in the film in different capacities, a racial analysis around the issues covered in the film is non-existent.

Race is a huge factor when it comes to access to contraception and reproductive health care; over 60 percent of people who have abortions are people of color. Yet, it took 40 minutes for a person of color to share an abortion story. It seemed that five people of color’s abortion stories were shown out of the over 20 stories, but without actual demographic data, I cannot confirm how all the film’s storytellers identify racially. (HBO was not able to provide the demographic data of the storytellers featured in the film by press time.)

It’s true that racism mixed with sexism and abortion stigma make it more difficult for people of color to speak openly about their abortion stories, but continued lack of visual representation perpetuates that cycle. At a time when abortion storytellers themselves, like those of NNAF’s We Testify program, are trying to make more visible a multitude of identities based on race, sexuality, immigration status, ability, and economic status, it’s difficult to give a ringing endorsement of a film that minimizes our stories and relegates us to the second half of a film, or in the cases of some of these identities, nowhere at all. When will we become the central characters that reality and data show that we are?

In July, at the progressive conference Netroots Nation, the film was screened followed by an all-white panel discussion. I remember feeling frustrated at the time, both because of the lack of people of color on the panel and because I had planned on seeing the film before learning about a march led by activists from Hands Up United and the Organization for Black Struggle. There was a moment in which I felt like I had to choose between my Blackness and my abortion experience. I chose my Black womanhood and marched with local activists, who under the Black Lives Matter banner have centered intersectionality. My hope is that soon I won’t have to make these decisions in the fight for abortion rights; a fight where people of color are the backbone whether we’re featured prominently in films or not.

The film highlights the violent rhetoric anti-choice protesters use to demean those seeking abortions, but doesn’t dissect the deeply racist and abhorrent comments, often hurled at patients of color by older white protesters. These racist and sexist comments are what fuel much of the stigma that allows discriminatory laws, such as those banning so-called race- and sex-selective abortions, to flourish.

As I finished the documentary, I remembered a quote Chelsea, a white Christian woman who chose an abortion when her baby’s skull stopped developing above the eyes, said: “Knowing you’re not alone is the most important thing.”

In her case, her pastor supported her and her husband’s decision and prayed over them at the church. She seemed at peace with her decision to seek abortion because she had the support system she desired. Perhaps upon seeing the film, some will realize that all pregnancy decisions can be quite isolating and lonely, and we should show each other a bit more compassion when making them.

My hope is that the film reaches others who’ve had abortions and reminds them that they aren’t alone, whether they see themselves truly represented or not. That we who choose abortion are normal, loved, and supported. And that’s the main point of the film, isn’t it?

Abortion: Stories Women Tell is available in theaters in select cities and will be available on HBO in 2017.

Culture & Conversation Media

From ‘Mouseburger’ to Media Icon: Bio Traces Rise of Cosmo Editor Helen Gurley Brown

Eleanor J. Bader

Helen Gurley Brown was a publishing giant and pop-culture feminist theorist. But according to her latest biographer, she was a mass of insecurities even as she confidently told single people, especially women, to take charge of their sex lives.

Like all of us, Cosmopolitan magazine’s longtime editor Helen Gurley Brown lived with conflicting drives and desires. But Gurley Brown’s ideas and insecurities had a public platform, where she championed sex for singles while downplaying workplace sexual harassment and featured feminist voices while upholding the beauty ideals that made her own life difficult.

A workhorse who played hard, Gurley Brown, who died in 2012, is presented as an often contradictory heroine and an unexpected success story in journalist Gerri Hirshey’s new 500-page biography, Not Pretty Enough: The Unlikely Triumph of Helen Gurley Brown.

Helen Gurley Brown’s life and example—almost a classic Horatio Alger “rags to riches” tale—affirms that the American idea of surmounting humble origins is sometimes possible, if improbable. But Gurley Brown’s story also illustrates both personal grit and endurance. Wily, willing to take risks, and sexually audacious, she might be a questionable role model for 21st century women, but her amazing story, as told by Hirshey, will nonetheless inspire and entertain.

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Born in 1922, Gurley Brown led Cosmopolitan for 32 years. She moved the magazine, which had been published continuously since 1886, from relative obscurity into the limelight. Known for its brash cover chatter and how-to articles on heterosexual man-pleasing, Cosmo is the world’s highest-selling women’s magazine, with 61 print editions. Its long history—alongside Helen Gurley Brown’s personal story—offers a fascinating window into the intersection between U.S. publishing and burgeoning 20th-century feminist ideologies.

Hirshey (whose earlier books include Nowhere to Run: The Story of Soul Music and We Gotta Get Out of This Place: The True, Tough Story of Women in Rock) presents Gurley Brown as a mess of pushes and pulls: insecure, brilliant, bold, self-effacing, loyal, independent, jittery, and frugal to the point of deprivation. Indeed, Hirshey’s revealing and detailed biography describes the pioneering editor as someone hungry for experiences; a sophisticated New Yorker with deep roots in rural America; and a writer of guidebooks who had trouble taking advice. In short, Helen Gurley Brown was limited by a host of personal issues, but that did not stop her from trying to push societal boundaries and shatter sexual propriety.

A native of small-town Arkansas, Helen’s childhood was marred by tragedy. Her father died in an accident when she was 10; several years later, her older sister, Mary, contracted polio, which left her partially paralyzed. Helen’s mother, Cleo, was overwhelmed and often depressed. Nonetheless, she scrambled to keep the creditors at bay, and the family lived in numerous decrepit rentals during Helen’s childhood.

Poverty was not the only obstacle Helen faced. According to Hirshey, “By the time Mary and Helen were school age, Cleo had begun her steady warnings that pretty girls got the best in life.” While Cleo never used the word “plain” to describe her offspring, it was clear that she did not think them comely. Helen was devastated. What’s more, the fear of being unattractive dogged her for her entire life and she had multiple surgeries to correct “flaws.” She also starved herself and exercised compulsively—and would likely now be labeled as having an eating disorder—to keep her weight at an unwavering 105 pounds.

Her success, Hirshey writes, was the result of luck, tenacity, and sheer chutzpah.

It started in the 1940s, shortly after she finished high school and secured the first of a string of secretarial jobs. During her tenure as a typist and stenographer, Helen cozied up to her male bosses and slept with some of them.

“It was the first time she truly observed and understood that sex is power,” Hirshey writes. “Helen had come to realize that sex was a surprising and thrilling equalizer between the sheets.” Gurley Brown pooh-poohed the idea that people should wait until marriage to have sex and had no problem dating men who were cheating on their wives. The same went, Hirshey writes, for racists and overt anti-Semites. Since she was giving a large part of her earnings to her mother and her sister, it was the size of a man’s bank book, rather than his politics, that evidently curried her favor.

Nevertheless, being a mistress had a downside, and Helen’s diary reveals that she felt like a “little bird … expected to stay in her cage, always available yet always alone.”

Her fortunes turned shortly after her 26th birthday, when she became secretary to Don Belding, chairman of the board at prestigious ad agency Foote, Cone, and Belding. Belding paid Helen $75 a week and treated her like a long-lost daughter; she considered him a surrogate father.

Alice Belding, Don’s wife, took a particular interest in Helen and, after reading something she’d written, persuaded her husband to give Helen a chance as a copywriter. He did, making her one of the first women to break into the field.

Meanwhile, there were men. Lots of men. “Certainly, men love beautiful women,” Hirshey writes. But Helen realized that when “the lights went out, Miss Universe might just as well be the poor, sooty match girl if she couldn’t make him shout hallelujah.” She loved the power sex gave her, but was hurt during a group therapy session when another participant dubbed her a slut. “Spoken with venom, it had the effect of a gut-punch,” Hirshey writes.  Still, it proved clarifying for Helen, allowing her to formulate the idea at the heart of her 1962 book, Sex and the Single Girl: There is nothing shameful about unmarried people having sex as long as it’s consensual.

Helen met David Brown, a high-profile movie executive, in 1958, when she was 36. David was 42, twice married and twice divorced, and had no interest in returning to the altar anytime soon.  This was fine with Helen. Nonetheless, as they spent more and more time together, they formed a strategic partnership. Yes, there was love, but Helen Gurley craved financial security, which David could provide. They wed in September 1959.

At that point, David suggested that Helen take a professional detour and write “a guidebook of sorts for single women.” Hirshey reports that he envisioned “something along the lines of ‘How to Have a Successful Affair’” and ticked off possible subjects, including how to snare a guy and dress for conquest. He also wanted the manual to include concrete sex tips. Helen loved the idea and the pair began to work on it, she as writer, he as editor.

Sex and the Single Girl told the truth as Helen saw it. Hirshey notes that the book was meant as a practicum, “and was never intended as an overtly feminist tract. Systemic change was not at all on her radar; she addressed herself to bettering the small, quotidian lives toiling within the status quo, of those, herself included, she would come to call ‘mouseburgers.’ Sexism was not even in her vocabulary.”

Her message was quite simple: Sex needed to be decoupled from marriage. As for gender roles, she was fine with women playing coy. In fact, she explicitly advised women to go out with men only if they could pay for everything, from dinner and drinks to “prezzies.”

There were of course, detractors, but Sex and the Single Girl sold millions of copies and made Helen Gurley Brown a household name. She appeared on countless TV talk shows and was the first woman featured in Playboy’s famous centerpiece interviews.

In the throes of her success, however, David was offered a job in New York and the couple decided to leave California, where they’d both lived for decades. David, Hirshey reports, knew that Helen needed to work, “that Helen unemployed would be Helen unhinged.” Together, they developed a prototype for a monthly women’s magazine that would popularize and expand upon the ideas in Sex and the Single Girl. They called it Femme and floated the idea to every publisher they knew. No one liked it.

Eventually, Hearst Corporation suggested “superimposing” the format on one of the corporation’s least successful publications, Cosmopolitan, with Helen Gurley Brown at the helm.

It worked, not only boosting sagging sales but catapulting “The Cosmo Girl” to prominence. Sexual freedom, Gurley Brown enthused, was in–but apparently only for heterosexuals, since the magazine rarely acknowledged the existence of same-sex relationships or bisexuality.

Nonetheless, the first few issues tackled then-risqué themes, as these titles suggest: “The Bugaboo of Male Impotence”; “I was a Nude Model (and This is What Happened)”; “Things I’ll Never Do with a Man Again”; “The Astonishingly Frank Diary of an Unfaithful Wife”; and “How to Make a Small Bosom Amount to Something.”

As the “sexual revolution” of the 1960s took hold, Cosmo flourished, albeit steering clear of covering racial unrest, the Vietnam War, or the counterculture and anti-militarism movements. Likewise, if Gurley Brown had any thoughts about the civil rights or peace movements, Hirshey neglects to mention them. She does note that for Helen, “readers of color scarcely registered.” It’s too bad this is not probed more deeply in Not Pretty Enough, and why the editor remained above the fray—was it fear, disinterest, or hostility?—remains unclear.

The women’s movement of the 1960s and 1970s did capture Helen’s interest, though, and she considered herself a devout feminist, with a particular passion for promoting reproductive rights. She wrote numerous articles about the need to overhaul abortion policies pre-Roe v. Wade, openly declaring that “it’s a shame that girls have to go to Mexico or Europe to be operated on.” At Cosmo, she cheered the arrival of the birth control pill in 1960; hailed the 1965 Supreme Court decision in Griswold v. Connecticut that gave married heterosexuals access to birth control; and was exuberant when Eisenstadt v. Baird gave unmarried couples the same right to control their fertility in 1972.

Sexual harassment, on the other hand, was befuddling to her. Remembering her days as a secretary, she dubbed slaps on the ass and sexually suggestive comments to be harmless fun. “When a man finds you sexually attractive, he is paying you a compliment,” she wrote in a monthly Cosmo column. “When he doesn’t, that’s when you have to worry.”

Small wonder that Kate Millett picketed Cosmo for its “reactionary politics” or that Betty Friedan slammed it for its sexism and preponderance of inane articles on keeping men happy.

Despite disagreeing with these thinkers, Helen Gurley Brown marched down New York City’s Fifth Avenue to celebrate the 50th anniversary of women’s suffrage in August 1970 and published articles written by prominent feminists as the 1970s unfolded.

Then, at the height of the AIDS crisis, Gurley Brown stepped in it. In early 1988, Cosmo ran an article that minimized the possibility of heterosexual transmission of HIV and made it sound as if straight women were immune from infection. Equally horrifying, the author, psychiatrist Dr. Robert E. Gould, was overtly racist. “Many men in Africa take their women in a brutal way,” he wrote, “so that some heterosexual activity regarded as normal by them would be close to rape by our standards.”

Oy. Readers were aghast, and Gurley Brown was roundly and deservedly criticized. Even Surgeon General C. Everett Koop weighed in, saying the article did “such a disservice” by suggesting that the risk of contracting the virus was low for heterosexual women. Hirshey reports that, inexplicably, the article was never retracted or corrected.

By this point, however, Helen was showing signs of dementia—she had periodical temper tantrums in public and was becoming less reliable and sharp—so Hearst Corporation brought in several new editors, albeit without firing Helen. She continued going into the office until shortly before her 2012 death. She had done paid work for 71 years.

Hirshey’s sources range from primary documents and in-person interviews with people who knew Gurley Brown, including Gloria Vanderbilt and Barbara Walters. Correspondence and recorded talks between her and friends such as Jacqueline Susann and Joan Rivers provide incisive, funny, and poignant anecdotes. These interviews give the book reportorial gravitas and intimacy. And although Hirshey had only a passing acquaintance with her subject—she had interviewed Gurley Brown decades earlier for an article about marriage proposals—she nonetheless manages to show Gurley Brown as a regular Jane who spoke openly about her nagging doubts.

Many readers will feel as if they can relate to Gurley Brown’s struggles and triumphs. Throughout the book, I felt sad for her, but also wished we’d met.

In fact, I closed the book wanting more; among other things, I wanted to better understand what it was like for her to move between near-poverty and the upper crust. Did she feel like an impostor? Did her lifelong conviction that she was not pretty enough or smart enough keep her from feeling connected to others? Did she ever feel truly secure?

Perhaps Gurley Brown’s self-doubts are what kept her from becoming arrogant or abusive to others; even those who hated Cosmopolitan or were frustrated by her racial and political blind spots admired her kindness. Similarly, these doubts did not prompt her to disguise her eccentricities—among them, pilfering from petty cash and always taking public transportation rather than cabs. Indeed, whatever Gurley Brown felt about her own appeal, Hirshey’s biography presents Helen Gurley Brown the woman as quirky, humble, and utterly fascinating.

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