Crossing · A Memoir · Deirdre N. McCloskey
The University of Chicago Press

McCloskey crossing

"McCloskey, married for 30 years, the father of two, and an economics and history professor, was a secret crossdresser for 41 years, as 'Jane.' At 52, he realized that his real identity was as a woman and began transitioning as 'Dee' to become 'Deirdre.' At the heart of this fascinating and poignant story, told in the third person, are the two years (one in Holland) of hormones, multiple surgeries, electrolysis, and a legal name change, all part of the physical and emotional 'crossing' from male to female. The big-boned Deirdre describes the joy of 'passing,' the fear of being 'read,' and the occasional loving support she has received in contrast to painful estrangement from family, friends, and colleagues. . . . Revealing, humorous, and provocative."—Library Journal

"A searing tale of the traumas and rewards of gender change. . . . A powerful indictment of legal, medical, and institutional obstruction."—ForeWord
Crossing is not only about the physical change from male to female, but also about the cultural difference it can represent. For those who have come of age in an era impatient with gender stereotypes, this may be the most provocative part of the book. Are men and women really different? Below—from one who has been both—a summary of the differences.

Deirdre's List of Differences

  • She catches falling objects quicker.
  • She is more easily startled by loud noises or sudden movements.
  • She cries.
  • She sweats less.
  • She sleeps more and she sleeps better.
  • She stutters less. Or so people tell her.
  • She loses weight less easily.
  • She chooses clothing with an eye, imagining outfits from her closet or the store rack, and can judge instantly when trying them on whether they work.
  • Her color memory and color vocabulary are a little better.
  • She works at remembering what people wear.
  • She remembers neighborhoods better, without effort, and in driving she starts to navigate by landmark and feel rather than by direction and map.
  • She likes cooking.
  • She listens intently to stories people tell of their lives, and craves detail.
  • She is willing to listen to painful stories of sickness and personal catastrophe.
  • She is more alert to relational details in stories: Ah, I see, she's his cousin by marriage. She finds herself remembering the family trees, the ex-boyfriends, the big events.
  • She has gotten no more skillful at telling stories.
  • She is worse at telling jokes.
  • She is less single-minded.
  • She is therefore less one-tasked.
  • She is less impatient.
  • She drives more slowly and less aggressively.
  • She can't remain angry for long.
  • She feels duty bound to wash the dishes.
  • She loves, just loves, the little favors of womankind, getting a card for someone, making meatloaf for Charles up the street, helping someone through a day of his life.
  • People treat her more kindly. A woman is less threatening and gets smiled at more.
  • On the other hand, she is treated more casually. Clerks and bureaucrats do not expect trouble from a woman. They are not on guard.
  • She assumes a less confident mask for dealings with salespeople and auto mechanics.
  • She has stopped paying attention to guy things—such as cars and sports and war stories.
  • She is uninterested in sports and finds the sports pages pointless.
  • She no longer thinks of social life as strict exchange.
  • She dotes on every child she meets.
  • She reads women novelists, for years only women novelists.
  • She takes the woman's side.
  • She is religious.
  • She is neater, her cleaning lady notes, and Deirdre herself notices her determination to make the bed as soon as she gets out of it.
  • She has more friends.
  • She looks on men as sexually interesting and emotionally stupid.
  • She thinks less about sex.
  • She cares about love.
  • She gets as much pleasure from loving as from being loved.
  • She cares about relationships and devotes sustained thought to them.
("Deirdre's List of Differences" is adapted from Chapter 45, "Differences")

Posing as the opposite gender is easy in cyberspace, right? Joshua Berman and Amy Bruckman at Georgia Tech are putting this assumption to the test in the Turing Game. If you participate, you might wind up in Joshua's dissertation.


Before Deirdre there was Jane

The big event of that half week was on the way home from the East Coast to Iowa City. Donald had arranged to stop in a Chicago suburb for Saturday night, going to a motel to meet his crossdressing friend Lucy. Then they planned to navigate the parking lot of the motel next door to attend their very first crossdressing meeting.

The meeting was for the Chicago chapter of Tri Ess, the national crossdressing sorority, which Donald had joined through his Chicago BBS girlfriends. He had been excited for weeks and planned it like a military campaign, lugging from Iowa City to Philadelphia to Baltimore to Chicago a big suitcase filled with his outfit for the evening and his Philadelphia loot. He chose his Marilyn Monroe wig and a black crepe dress inherited from his wife.

Lucy arrived already dressed, and Donald complimented him, as women do: "You look great!"

"I found a cosmetician in my suburb who does makeovers on crossdressers." Lucy looked like a suburban housewife, not a drag-show star. Later Donald bought some dresses at the woman's store and had a makeover himself. The cosmetician's youngest son was a drag queen and competed in beauty contests.

Lucy got anxious and wanted to go, and Donald/Jane agreed as he struggled into the dress, a little small: "I'll come over when I'm ready. Zip me up, will you?" Better to go by myself, he thought. The probability of being read rises with the square of the number of crossdressers in a group. (One is "read" like a book, detected in the wrong gender.) The man on the street reads the least convincing one of a group and then notes that all these women seem large.

Stepping out into the hallway of his motel half an hour later he was frightened, imagining detection and the punishment of scorn. On the stairs going down, avoiding the elevator with its long looks, he walked by a couple coming up, but they didn't appear to read him. Clicking in heels around the back of his own motel, he walked into the open toward the other one. It was Donald's first time out-of-doors as a woman, apart from a very few nighttime walks in empty streets in Princeton and Chicago. It felt natural. He hitched up his skirt and leaped over a little stream between the two motels, scuttling through the other parking lot in full drag in the glare of the late afternoon sun. Still outside, as he approached the entrance to the meeting room he encountered a woman: Oh, oh; she'll read me. Wait: no. It was another crossdresser on his way to the meeting. Easy to read when you're looking for it.

When Jane came into the meeting room it was filled with crossdressers, and his first impression was, These women are huge! They were a third bulkier than a roomful of genetic women. It seemed to him that the average crossdresser was above average in height. Can't be. (It can, though. If there is a deficiency of testosterone in adolescence the bones do not close off early in their growth. That's why boys who mature early tend to be short and why the castrati playing women's roles with women's voices in early opera were unusually tall for men. Not that there's any evidence of testosterone deficiency in crossdressers, mind you. Just guys.) Still, the clubs ordinarily do not have really big men in them, which makes one wonder how the bigger crossdressers and gender crossers are able to express themselves. Perhaps in football.

Most everyone was cordial, though some of the prettier ones seemed snooty. Jane later met one of the snooty ones in Atlanta at a conference discussion on gender-crossing life for professionals and found him shy and uncertain about his future. They all had name tags, and Jane spotted and hugged Suzy, one of the BBS friends he had not met in the flesh. Suzy was "Susan Roberts," which is to say that in the convention of choosing feminine names among crossdressers he was "Bob" as a man. He was tall, thin, blond, breaking up with an intolerant wife whom he still loved, and struggling with his identity.

"I went to therapy for two years with my wife," Suzy said.

"Two years. Did it help?"

"In a way. We're getting divorced. The therapist finally said to me, 'Look: your wife is unable to adjust. Some women can handle it, others can't. She has her own reasons.'"

When the official meeting broke up Jane was standing next to a vivacious crossdresser named Robin, a little taller than he was, with a Chicago-accented voice. He was brassy, intelligent, extroverted, complaining knowingly about the administration of Tri Ess. (Jane learned later that it was his first meeting too.) He proposed that he, Jane, Suzy, Jane's friend Lucy, and another crossdresser go out on the town. Lucy demurred, and the remaining four musketettes set out for a lesbian bar.

The tougher straight bars are good places to get killed. Gay bars also have the undercurrent of lethal violence that is the male condition. The lesbians are more civilized and don't mind having crossdressers around, regarding them as harmless. The first place was quiet, though enlivened by the crossdressers (ten of them, others from the Tri Ess meeting, crowded along a set of bar tables like a typing pool out for an after-work drink) and then by an ineffectual fistfight between two lesbians in a love triangle. Jane danced the way the kids do, by himself, different from the lovely paired regularity of square dancing. A butch dyke paired with Jane for a while on the dance floor, and Jane gave himself over to ecstasy. "Just dance!" the dyke said, "Don't come on to me." When he had to go to the bathroom Jane had the others take a picture of Suzy and him outside the "first ladies' room." Pictures are big among crossdressers. How many crossdressers does it take to go the ladies' room? One hundred: one to go and ninety-nine to take pictures.

They went to a much hotter lesbian bar called Temptations on Grand Avenue in the Chicago suburbs. It was in a strip mall next to a tire store, and when the stars came out it glittered. Robin had been to the place before, as everyone else had too. They regarded Jane as bold to go with the girls barhopping on her first night out. What made Jane run? Square dancer, middle-aged college professor, father of two, thirty years married, pillar of the community shook to the beat of the drum with a hundred others of assorted genders and sexual preferences. The cool dance the kids were performing turned out to be steps that Donald had learned the year before at a square dance in Iowa City. The company was diverting, and each set was long.

Robin introduced Jane to a lesbian sitting at a little table crowded with others. She looked like a suburban woman. Kids. Van. She was in her forties, dressed butch but not too. Acceptable in the mall. Though women can get away with more.

"I was married and have grown children," she told Jane. "I only figured this out a few years ago."

"How have they adjusted? I mean your family?" Jane was always interviewing people, gathering data like some sort of anthropologist, an anthropologist who could go native.

"Poorly." It was not unusual news. In the gay and lesbian community, Jane read later, they spoke of 80 percent: 80 percent of your family and friends eventually adjust, perhaps after years of rejection, and go on loving you after a fashion. That leaves 20 percent. As they talked about rejection and acceptance Jane warmed to her, and he found himself flirting as the femme. They danced for a while to the throbbing music, then she bought Jane a beer. In his three later visits to Temptations Jane looked for her, a regular it was said, but never saw her. Jane/Donald was still unclear about his preferences. Gender crossing is a matter of identity, not affectual preferences. A third of post-op transsexuals go on loving women, he would remind himself out of his new learning. Not that I'm a transsexual.

He went to Temptations only those three more times. Chicago is 240 miles from Iowa City. (Deirdre would explain to Dutch people where Iowa City was: "Near Chicago." Oh, how far? they would ask, supposing she meant 50 kilometers. "It's 500 kilometers due west, as far as Amsterdam is west of Berlin. Not too far.") Donald never did go to similar places closer to home. Fear, security, the closet.

Robin said later that he was struck that first time by Donald's reaction as Jane to the unbuttoned scene. Jane came up to Robin and gushed, "Lord, I just love this!" The gushing seemed to Robin significant, signaling more than a guy in a dress. Robin was coming to terms with his own gender crossing and went full time the next month, just before Donald's dam broke. Robin had the operation in Montreal a couple of months after Deirdre had it in Australia. Deirdre called Robin afterwards and they talked about how they just loved this.

He got back to the motel room at 3:00 a.m. and had a 10:00 a.m. flight home. That afternoon in Iowa he was teaching business economics in his macho, I'm in charge style. As men brag about their little exploits, he dropped hints to the kids about his wild night at a bar in Chicago. He left out the detail that he had danced through it in a cocktail dress.

He went to the first meeting of his local club, Iowa Artistry, thrilled and frightened. The meeting was held in a big motel out by the interstate. He was pleased to drive across town dressed—This is how it feels to be a woman—but nervous about coming into the motel as Jane. In fact respectable motels are cordial to crossdressers, because they are good customers. Aside from makeup on the towels, they are no trouble. They don't drink much, and they don't do sex or violence.

Iowa Artistry was forthrightly Iowan. The meeting was like a Kiwanis Club in drag, with reports from the treasurer and mild quarrels about governance. Jane had long, earnest talks about living with crossdressing. His attention was held by a thirty-something gender crosser named Anna who worked as a technician in a corporation south of Iowa City. She had been full time for a year and had finished electrolysis on her beard down in Dallas, which he quizzed her about. She was intelligent and sympathetic, once married, kids. Donald was deliberating, unaware. But of course I am a heterosexual crossdresser. Just wondering.

Donald's wife dreaded people's finding out and was appalled that after the meeting a group of fifteen or so went on to a local bowling alley. Nothing happened, no one found out. One attempt at rolling the ball left Donald/Jane's false thumbnail halfway down the alley, and he had to walk out to retrieve it, amused and embarrassed. He watched closely another crosser, very effeminate. She was there with her male lover, the two making an ordinary husband and wife. Three years later she had her operation and they were legally married. She worked as a telephone operator. The daily practice and her determination had made her voice good. The heterosexual crossdressers, by contrast, were breezily male in their voice and behavior. Jane didn't think much about where he fit in.

There was only one other group in the bowling alley, at the opposite end. Eventually one of them came over to see what was going on, and a crossdresser replied with a smile that they were a "mixed league" of bowlers—a man and a woman in the same body. When crossdressers meet straight people in a group it works fine. Crossdressers call it "gender education."

("Before Deirdre there was Jane" is excerpted from Chapter 5, "Clubs")

Square dancerIn dragGood hair day
Images left to right: Square dancer, 1994; In drag, 1995; A good hair day, 1997

Copyright notice: Excerpted from pages 28-32 and 255-61 of Crossing: A Memoir by Deirdre N. McCloskey, published by the University of Chicago Press. © 1999 by the University of Chicago. All rights reserved. This text may be used and shared in accordance with the fair-use provisions of U.S. copyright law, and it may be archived and redistributed in electronic form, provided that this entire notice, including copyright information, is carried and provided that the University of Chicago Press is notified and no fee is charged for access. Archiving, redistribution, or republication of this text on other terms, in any medium, requires the consent of the University of Chicago Press.

Crossing: A Memoir
by Deirdre N. McCloskey
© 1999, 280 pages, 32 halftones
Cloth $25.00 ISBN: 0-226-55668-9
Paper $15.00 ISBN: 0-226-556697

For information on purchasing the book—from bookstores or here online—please go to the webpage for Crossing.