In 1870, when Henry and Pauline Durant founded Wellesley College, gender was simple. You were either male, in which case the ivy-fringed bounty of American higher education lay at your feet, or female, in which case your options were confined to a few women’s schools. Now, in 2014, most previously male universities are co-ed, and gender is complicated. The traditional women’s college looms out of the past like a dinosaur.

Evolving the dinosaur requires a fluid understanding of gender, one that embraces transmen and transwomen as well as everyone in between. As the New York Times reported last month, single-sex colleges are struggling to work out where their loyalties lie. The ideological masonry of these schools rests on progressive assumptions about inclusion and empowerment, but they were also designed with specific beneficiaries in mind: women. So who counts as a woman? And is it possible for colleges to draw that line without tarring their missions of tolerance?

The topic hits home for me—I sat in all-girls classrooms every weekday from fourth grade through senior year of high school. My mom was the one who insisted on giving her daughters a single-sex education, where they wouldn’t be distracted by boys or taught they were somehow less than. Shy in a lot of contexts, I’ve never been shy in class, and I thank a history of all-girls labs and study halls for that. As much as I want the advantages of women’s schools spread widely, I feel protective of these institutions’ founding goals.

There are two good starting points for understanding transgender admissions at women’s schools. The first is that most colleges claim to evaluate applications on a case-by-case basis (so, few definite policies). The second is that, in practice, transwomen face a tougher path getting in than transmen. This last point is hard to wrap your brain around: Male-to-female undergrads will suffer as much as, if not more than, their cis peers from patriarchal influences on education (male students get called on more in class, for instance), and they possess a keen and unique understanding of both gender and discrimination. If single-sex colleges exist to embolden women while giving students the benefit of diverse perspectives, transwomen seem like the pedagogical holy grail, their claim to belonging a no-brainer.

Yet for many schools, it hasn’t always been so obvious. Last year, the widely publicized attempt of one transwoman, Calliope Wong, to apply to Smith College loosed a tide of institutional soul-searching. Wong was rejected because not all of her application materials reflected her femaleness—while she was able to submit transcripts and recommendations that identified her as a woman, her FAFSA (a federal financial aid form) pegged her as male. Obtaining legal, government-anointed proof of womanhood depends on more than supportive parents and high school administrators. To alter the sex designation on your birth certificate or passport, you might need a sex-change operation—a huge hurdle for a 17- or 18-year-old student just awakening to her gender identity. Wong gave up, but her story ignited outrage both on and off campus, and the next January, Smith unveiled a new admissions policy: No longer would federal forms like the FAFSA belong on the list of documents needed to “consistently reflect the candidate’s status as a woman.”

But after that initial spurt of progress, the conversation stalled. Student activists pressed the admissions office to go further, arguing that, instead of requiring any sort of consistent female identity on academic forms and recommendations, Smith should simply ask high school seniors whose materials showed a gender discrepancy to submit a supplement explaining why. As many have contended, it’s not always easy for transgender applicants to get their high school teachers and administrations to refer to them as women, especially when they’ve grown up male. And throwing prospective Smithies at the mercy of possibly biased communities seems unfair. A transgender freshman told BuzzFeed: “Thinking your average high school can just do that is a total fantasy. They say all we need is for all the gender markers to be consistent, but they don’t really acknowledge what really goes into that and how hard it is.”

Smith’s “consistent identifier” policy flows from an interpretation of Title IX that scholars have since refuted. (And their qualms are now official: In April, the Department of Education released a statement declaring transgender students protected under affirmative action law.) Yet as of late last month, the college still seems inhospitable to the supplement option. Smith’s director of college relations Sam Masinter confirmed the ongoing requirement “that each candidate’s materials reflect her status as a woman.” He forwarded a memo senior administrators had sent to student activists after a meeting on Dec. 6. “The admission of male-to-female transgender students to women’s colleges is a complex and evolving issue,” it read. “It’s one on which people of good intent, inside and outside the Smith community, hold a range of views. At Smith, in both admission and campus life, we are focusing on the broad policy challenge of how to be supportive of students who are exploring gender identity while at the same time remaining deeply committed to our mission as a women’s college.”

Meanwhile, in the halls and dorms of that women’s college, support for transwomen is growing. “ ‘Women’s college’ is a bit of a misnomer,” says Julia Marciano, a Smith undergrad who advocates for male-to-female students at her school through a group called Q&A. “They’re places for minority genders, where those genders can flourish, learn, and feel safe.” While a “small group of exclusionary radical feminists” at Smith feels threatened or diminished by the presence of transwomen, she continues, that viewpoint “misunderstands the lived experiences of transpeople. It says, ‘I don’t want men at my college,’ but it’s not men who are applying. It’s women, with experiences of being women.”

Marciano has a powerful if obvious rejoinder to the argument that transwomen might alienate their classmates with their sex-based entitlement. “Some people might say, ‘I don’t want someone with male privilege coming to my institution, walking around like the boss,’ ” she tells me. “But that’s grossly not true! Transwomen face so much more discrimination than ciswomen do. The murder and crime statistics against them are terrifying.”

Marciano may be on the vanguard, but the bigger caravan of women’s higher education is lumbering along in her wake. Simmons College in Massachusetts recently accepted a transwoman, Alex Sennello, who told me she was drawn to the school because of its “strong focus on social justice and feminism” (though she ultimately decided to attend the co-ed University of Illinois). Sennello did not disguise her transgender identity in her application, and her Simmons acceptance letter praised her activism on behalf of the LGBTQ community. “I feel like including that [praise] in the letter was code,” she said.

Cryptic language pointing in the eventual direction of acceptance seems like the new normal. “Given explorations and discussions that we have begun and will continue to undertake in the coming year, we are not prepared at this time to provide a definitive answer that would preclude or encourage any given admission request,” wrote a spokeswoman from Scripps College in Claremont, California. Yet “we believe that our mission includes empowering those who face gender discrimination, and is thus inclusive of trans* identities.”

Likewise, Marilyn Hammond, interim president of the Women’s College Coalition, explained in an email that she could offer little “specific information” on the topic, and that she knows of no “norm or typical policy” schools have embraced. But “I do know that women’s colleges value diversity and inclusion and take seriously their commitment to provide a supportive environment for all students academically, psychologically, and socially,” she finished.

“We don’t really have policies,” Barnard’s president, Debora L. Spar, informed the New York Times. Despite that, Barnard just appointed a brilliant transgender woman to a prestigious professorship.

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Meanwhile, transmen are making their own forays into all-girl institutions. The challenges they encounter, though, have less to do with eligibility and more to do with fitting in once they arrive.

From an administrative perspective, these men should be all set. While female-to-male applicants must apply as women, Scripps, Smith, and Bryn Mawr explicitly state that any student who completes the graduation requirements, regardless of gender identity or expression, is qualified to receive a degree. A student could transition during his time at the college and would never be asked to leave for it. Colleges without written policies on transmen still accommodate admitted students who weave between masculine and feminine selves. Mount Holyoke reissues diplomas for alumni who’ve changed their names and sexes after graduating. Former Barnard President Judith Shapiro pledged commitment “to the individual needs of students who, once at Barnard, undergo a gender transition” (though the school later drew fire for denying one female-to-male freshman’s request for neutral housing). At Wellesley this spring, senior Alex Poon made history by winning the 119th annual hoop-rolling race. Poon, a computer science major from Virginia, is the first transgender student to seize that glory—with some help from genetics: His mom was also a Wellesley hoop champion.

Poon’s case, though, seems subtler than Wong’s. While Wong felt deeply that she was female and wished to learn in the company of other women, Poon identifies with the demographic—men—that Wellesley keeps out. Trickier still, Poon knew he was a man long before he sent in his application. On the phone, he spoke of the “biological loophole” he’d “capitalized on” in order to go to a women’s college so that he could, in his words, “understand how to be a guy.”

Women’s colleges offer a measure of physical safety that co-ed institutions cannot. Poon, a self-described “gym rat” and the captain of his all-girls high school swim team and the men’s water polo team at an affiliated boys’ school, is pretty tall and athletic. If he weren’t, he says, “I’d worry about getting hurt. Whether you’re male or female, you run the risk of making yourself vulnerable [at a co-ed school].”

And beyond the safety angle, the case for welcoming transmen at women’s colleges has a lot of merit. If the unique mission of a single-sex school is to nurture and empower minority genders, then surely transmen are natural candidates for inclusion. These institutions have always been bastions of nonconformity and social justice. Plus, the entire business of shutting out female-to-male students smacks of a conservative, stifling vision of the sexes—one in which you either belong to the right club or don’t. Still, a question lingers: Why seek out a women’s college if you object to strict gender binaries?

The arguments against transguys at women’s schools (colleges make a point of not tracking the data, but Poon says around two or three Wellesley students transition every year in a given class) orbit around phrases like “female self-determinism.” A Facebook group (now inactive) called “Keep Mount Holyoke, Wellesley, and Smith Single Sex,” asserted that “Becoming a man and remaining at a women’s college is analogous to renouncing your citizenship, yet expecting to maintain the benefits of citizenship. There is a limit to tolerance and acceptance; there is a point at which Mount Holyoke, Wellesley and Smith must demand that their mission be respected.” In talking to people for this piece, I heard the claim that women’s colleges exist not to foster independence and freethinking in all marginalized groups, but in one very specific marginalized group. Thus, Wellesley doesn’t admit black men even though they’ve dealt with discrimination and could bring valuable perspectives to the table. That seems reductive, but as a girls’ school alum, I get it. If you’ve jumped ship into maleness, perhaps you surrender your right to inhabit an all-women’s world. (Or at least, if you want to take classes in the chambers of femininity, you have to go through the usual cross-registration routes.)

But these philosophical quandaries may matter less than the practical realities of being one of the only guys at a girls’ college. Transmen surrounded by women face a unique set of perks (especially if they’re straight) and challenges. For a female-to-male friend of mine (not a college student), socializing with women right after his transition felt safe and familiar, but hanging out with dudes was necessary to help him learn the ropes of male gender presentation. And in single-sex environments, there’s a sense of loneliness. Poon spoke regretfully of small alienations and points of disconnect: “People don’t mean to be rude, but sometimes it just comes out. They’ll be like, ‘Oh, that’s so male of you, of course you want to eat cheeseburgers all day.’ ” In his telling, microsignatures of difference often arise: Someone will toss out a “Bye ladies, see you tomorrow.” Or he’ll have to run all the way across campus to find a bathroom.

Yet the picture Poon paints of life at Wellesley includes acceptance and support. “I feel very embraced. The community here is very unique,” he says. He explains about societies, which are the Wellesley version of sororities, except they have a more academic focus. Poon burned to join the group Alpha Phi Sigma but felt that he couldn’t because one of its pillars was “sisterhood.” “It had been founded forever ago,” he told me, and had a hallowed, traditional aura. Poon didn’t want to make people uncomfortable, so he put his hopes aside until they spilled out, unbidden, during a conversation with a friend in Phi Sig. “She told me, ‘Alex, we have a position open for a special male member,’ ” he recalls. Normally the lucky guy, called the Phi Sig “knight,” attends Harvard or MIT; his duties include going to parties with the girls and generally serving as a kind of brother. Poon applied for the spot alongside this year’s crop of illustrious Cambridge gentlemen and won.

“For my peers to be so accepting of me in such a public way felt amazing.” Poon recounts.

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I badly wanted to end this article on that image of inclusion. It reminded me of the final scene of an uplifting movie: The hero, embraced for who he really is, wins the tournament and restores our faith in the universe. Except the opening predicament still looms. Who counts as a woman? Someone who has felt intensely for as long as he can remember that he is male?

Students like Poon expose the atavism of single-sex colleges, which grew up around a definition of gender that completely ignored the transgender community. Now, these schools’ founding principles—a dedication to specifically female flourishing—dictate that they discriminate against transmen for belonging to the wrong minority gender, and sometimes transwomen for being born men. The solution to the transwomen problem is clear: Admit them! But one can’t ignore how the solution to the transmen problem—accepting them as “women”—either cancels out how these students have chosen to define themselves or broadens the definition of “woman” so far as to render the entire single-sex project meaningless.

Perhaps it is. What the logic of women’s colleges fails to take into account is that every woman at Wellesley exists on a spectrum between female and male. For administrators to see the requisite womanhood in a man named Alex but not in, say, a guy who likes to cross-dress, or a guy who doesn’t play sports, or any guy right up to Rambo at the very edge of the continuum, seems nonsensical. In the rightful pursuit of justice, tolerance, and inclusion, these schools must flaunt their own contradictions, must basically admit that they’re running on ideological fumes. Yet protecting their raison d’etre (which is to nourish exclusively women, at the expense of all nonwomen) by keeping out transmen appears to be a bargain they aren’t willing to make.

What should they do? If women’s colleges have any hope of surviving our cultural gender breakthrough, they have two options. They can either insist on drawing an arbitrary line, which would force them to discriminate against minorities their founders never dreamed of, or they can decide to prioritize the ideals on which they were originally based: diversity, empowerment, tolerance. If they choose the second route, the obvious precedent would be historically black colleges, which now admit students from all racial backgrounds. These schools offer curricula geared toward the black experience. Students who apply realize that they are seeking out an education concentrated on a particular set of issues and sensitivities (and a student body that is predominantly black); likewise, Wellesley 2.0 might admit everyone but make it clear they are in the business of dispensing a feminist education.

To be sure, some advantages of single-sex schools would then be lost. There are women who go to all-female colleges because they have suffered sexual violence and don’t feel safe around men. There are women who go because they don’t want men shouting them down in class or Hoovering up all the professor’s attention. Yet many of these concerns could be short-circuited by the careful training of teachers, the social conditioning that comes with living in a feminist environment, and the demographic realities of a student body defined by its interest in women’s issues.

Again, I went to an all-girls school—the same one that Alex Poon attended before he shipped off to Wellesley. My nine years there were empowering and wonderful, and I loved them. But the practice of segregating male and female students leans on fraying and outdated assumptions about gender. It’s time to open up feminist spaces to everyone, and to integrate feminism more fully into the co-ed spaces we have. The dinosaur of single-sex education is faltering. Let it die.