It’s been a long time now since, at age 53, I became a woman. Actually, I’m an old woman more than twenty years on, who walks sometimes with a nice fold-up cane, and has had two hip-joint replacements, and lives in a loft in downtown Chicago with 8,000 books, delighting in her dogs, her birth family, her friends scattered from Chile to China, her Episcopal church across the street, her eating club near the Art Institute, and above all her teaching and writing as a professor. Or, as the Italians so charmingly say, as una professoressa. Oh, that –essa. She retired from teaching, though not from scribbling, at age 73, twenty years after transitioning, “emerita.” Not, you see, “emeritus.”

But of course one can’t “really” change gender, can one? The “really” comes up when an angry conservative man or an angry essentialist feminist writes in a blog or an editorial or a comment page. The angry folk are correct, biologically speaking. That’s why their anger sounds to them like common sense. Every cell in my body shouts XY, XY, XY! I do wish they would shut up. Wretched little chromosomes. In some magical future I suppose we’ll be able to change XYs into XXs. But not now.

And more importantly a gender changer age 53, as I was in 1995, can’t have had the history of a born girl and woman. She cannot have had the good and the bad experiences of girlhood and motherhood and the rest. No science can change her life history. It’s the same for a born female going the other way, to male—which by the way seems on recent evidence to be about as frequently desired as male to female. The singer and actress Cher’s son, for example. Neither way is all that frequent—maybe one in every 400 or so births. It is much less frequent than, say, gayness, with which it is chronically confused. Yet the desire to change gender is in fact vastly more common than the crazy guess in the dark ages of the 1960s that psychiatrists confidently proffered, of one in every 20,000 births. Upshot? You yourself probably know a transgender person, whether she has transitioned or not. When I first went to my little progressive Episcopal church in Chicago, there was someone going the other way, female to male, and a few years later another one.

Whoops, sorry, I’m drifting into statistics. An economist and historian who believes that many scientific questions, if not all of them, turn on “How Much” is liable to drift that way. But frequencies aside, a girl’s life is not the same as a boy’s, and I had a normal boy’s life, and the advantage in a macho field like economics of being a man for half of my academic career. The question of what you are is qualitative, not quantitative. What sort? What life? What team? In late 1995, I chose to switch teams.

I do not want to sound unreasonably essentialist. Genders massively overlap. We’re human or American or raised in Boston. People, whether male or female, born like me in the United States to white middle-class parents in 1942 share a great deal. It’s what makes high school and college reunions so nice, a renewal of old friends with so many old experiences in common. My mother born in 1922, says that she prefers to hang out with “people who danced to Harry James,” a 1940s bandleader.

My woman’s life since 1998, when Crossing, the memoir I wrote about my experience, finishes its account of the crazy three years 1995-1997 of my transition, has been that of a teacher and writer. . . and daughter and sister and girlfriend. Such a life in a free country can be achieved, aside from those pesky chromosomes and former life experiences. Thank God. Without the change I would have become by now a quite horribly miserable old man, enviously watching Oprah’s gender shows (Deirdre appeared on one in 2000) and the sweet and profound movie TransAmerica (2005) and Caitlin Jenner coming out in all her refreshed glory.

* * *

What questions, then, 21 years later?

Has your marriage-family come around?

No.

If you are one of the angry folk you will say, “Serves you right. You did a terrible, selfish thing to your wife. And your two grown children have righteously taken her side. Good for them.” A handful people have said such things to me, and a few more probably feel so. I guess my marriage family feels it still, two decades on. But I don’t know what is meant by “selfish” here. I guess the angry folk believe I changed for pleasure rather than happiness. Are those two the same? Worth thinking about, I reckon.

Or the angry folk say, “You were false, desiring to be a woman while married to one. You lied.” No I didn’t. I loved the love of my life truly and utterly normally and faithfully, and suppressed that other desire. People do, routinely. They’re complicated. It’s a Romantic fallacy to think that people have simple and eternal essences. They change. In a free society, shouldn’t they be allowed to? Tell me.

My wife soon remarried, and lives with her new husband and still enjoys the square dancing she and I loved in the last five years of our happy if sometimes tempestuous thirty years of marriage. Bless ‘em. She’s not spoken to me. In that autumn of first realization in 1995 I left to my wife—stupidly, husband-style—the task of telling my children, my grown son and my college-freshman daughter. Women do emotional work, Donald must have thought, if he thought at all, which I don’t recall he did. I should have gone myself in Donald drag to my children. Not that gender change is a theorem, to be “explained” with the snap shut of a proof. It’s a story, and in October 1995 it was in the middle of Act 1. But my confused and self-absorbed neglect was an awful mistake.

My daughter still lives in the Midwest; she is married and has a child. I’ve told in Crossing about how, a year later, when she was still in college, I saw her that one time, very early in my transition, a weeping father in a dress begging for a hug. My friend Patty had advised against the meeting, wisely. Later I occasionally wrote to her, fruitlessly, and a long time afterwards helped her financially. Her lone letter in reply said “Thanks for the money. I still don’t want you in my life.”

Why, my beloved, why, why? My love for your mother over a third of a century had nothing false in it. My love for you was unconditional. Still is. Why throw away love with both hands? Yet when I tell my sad story to girlfriends they sympathize, and then come out with their own family stories, of how Uncle George said something unkind to Aunt Jane decades ago at Thanksgiving, and they have never spoken since. It seems a common human story. An economist notes that love is scarce. The chances for love in this world are not unlimited. Better make the best use of them. Efficiency. Well . . . .

My son lives not too far from me. He too won’t speak. None of my marriage-family, out to cousins, is permitted to speak to any of my birth family, out to cousins. Is my son enforcing the embargo with threats? I don’t know. His wife’s father, a professor of law whom I persuaded once to meet me at O’Hare airport, won’t help, because he’s afraid of losing his daughter. To what? Not to love or to tolerance of human change. Hmm.

In 2000 I had moved from sweet Iowa City to a new job at the University of Illinois at Chicago, deciding to live downtown. I learned that a neighbor on the very same hallway was also a well-known libertarian, someone who wrote blazingly on human freedom. True, I noted, he and his wife were strangely distant towards me. Odd. I heard that every month the man hosted a soirée of free-market types. Oh, nice. Natural for me, I thought. But a note I left suggesting I might join got no response. Hmm. Oh, well. I’ve got plenty to do.

Then one day I learned with a jolt from another libertarian economist that my son came to the very same soirée, and knew that I lived thirty feet down the hallway. Good Lord. My Episcopal God was tapping me on the shoulder, hard. In the same hallway. Hope flared. Huzzah!! With the strange neighbor’s help, surely, I thought, I can get back my marriage family, my children, my grandchildren. After all, the neighbor believes in freedom. True, my son had chosen not to knock on the door down the hall. But, well, hope. I left a wrapped copy of Crossing at the neighbor’s door.

Next morning I opened my own door to get the newspaper. The package, unopened, lay on the welcome mat, a message scribbled on it, “We don’t want to have anything to do with you.” My breath stopped. I couldn’t cry. Hope left as shockingly quickly as it had arrived. I thought: So that’s why his wife so awkwardly wouldn’t let her children collect Hallowe’en candy from my door last October. Not even to indulge the sentimental middle-aged lady down the hall. So-called lady. Thus freedom. Maybe my son had claimed to them that I had been an evil father or something. I don’t know. By a decade later they had become at least ordinarily courteous in encounters on the elevator, and I invited them once by note to eat at my club. A note in return:

“No, we are your son’s friends.” And so?

I have not seen my son’s children, now in college or high school, or my daughter’s child, just now in school. The forbidding of children and grandchildren was at first like being stabbed in the chest, the knife twisted in the wound. Early on, I would send Christmas gifts to the grandchildren. But I gave up after a while. Strange, isn’t it, that I care about these offspring I’ve never seen? But there it is. Blood is thicker than water, I suppose.

What worries me most—with the decades, the stab wound hurts less—is the loss to my children and then their children. I would have been a good father, an aunt, whatever you want to say, and anyway a grandparent, nearby and visiting out of state. Youngsters benefit from having more people in their lives, more models of how to live and to love. Maybe my children think it’s catching. I have a lesbian friend who was kept from her beloved nieces and nephews on such grounds. No queers here. I had imagined I had raised my kids in liberal Iowa City to be liberals. Or even libertarians.

Both my children seem, the Lord be praised, so far as one can judge without contact, to be happy and safe, successful in their professions and good as parents. So perhaps I should quit whining.

One more story. I used very occasionally to drive by my son’s house. Nothing too creepy, understand, perhaps a half dozen times over fifteen years of a minute or so of mournful looking at the cute house they had on a quiet, tree-lined street in a gentrifying neighborhood, and then driving ruefully on. Once I caught sight of his shape through the blinds in the upstairs front window. Oh, my son, my son, my first born.

It turned out that the only mechanic who could service my charming little Smart auto—canary yellow with a black racing stripe—was located six blocks from my son’s house. One autumn day driving back from the mechanic, in a burst of courage, or a burst of the foolhardiness I exhibited in the old meeting with my daughter, I stopped and knocked on the front door. This is the time, I thought. It’s been twenty-two years. Be calm and loving.

No answer. The next-door neighbors were out in their front yard raking leaves. “They aren’t there now.” Uh, well, I’ll wait. “It’ll be two weeks! The house has been rented to a movie company for a set. The family went to a hotel.”

Gak. The one time I knock at his door, Hollywood intervenes. My Anglican God has a wicked sense of humor.

* * *

How are your relations now with your sister?

Excellent.

It took a few years. When she was chasing me around the country in the autumn of 1995 with clueless judges and prosecutors and psychiatrists in tow, she was having, I realized, her own problems. I joke that without her crazy attempts to prove me crazy the book would have been terminally boring: “I decided to change. Did. All is well.” (I also joke that I am the only person in most rooms who has been certified sane by psychiatrists four times. “As far as I know, everyone here is secretly a complete loony. Not me!”)

When I visited for three months in 2000 at the University of California at Riverside, close to Los Angeles, a Hollywood producer approached me about turning my memoir into a movie. Later a playwright colleague at UIC proposed a play. Not that either would actually have happened, given the odds. But anyway, drama needs conflict. My sister certainly provided it.

But in such a drama she would of course be the heavy. After the initial vanity-feel of the prospect wore off, I realized that I couldn’t possibly do that to my sister—the sweet little six-year old in 1959 in her rabbit-fur coat, she and my brother sung to sleep by their older brother’s folk singing in the 1960s, the grown woman in the 1980s a brilliant academic psychologist consulting her academic brother on the family business of professing. I love my sister and my brother. More of that thick blood, I suppose. (My brother, a playwright, never had much trouble with my change. He was like my cousin Phil, and so many other loving men.)

I forgave her after a couple of years. (I had forgiven her co-conspirator in the crazy autumn of 1995 by postcard, in about 1998. He was a professor I had caused to be hired at the University of Chicago. Once, showing a friend around the famous Department of Economics, I knocked on his door, but he became angry and would not talk. So strange are people, that if they do you damage, they remain angry. . . at you).

My sister and I for some years traded mollifying emails. She wouldn’t actually apologize, but invited me to a Christmas party in her Tucson home to which my mother, who lived then in New Hampshire and was a rock of love, wanting her daughters not to quarrel, was going to come. Yet later on the phone we quarreled, and she withdrew the invitation. I replied, “No. To hell with you. I’m coming, to see my mother,” and did, arriving from Chicago in the middle of the party. My sister was coldly courteous, as suited our mutual moods. Next morning I came out of the guest room, and saw her working on last-night’s pile of dishes. I saw, too, that the rug needed vacuuming, so without devoting much thought to the matter I found the vacuum and started running it. Then I noticed her looking at me strangely. I fancy that it was the first time she viewed me as an actual, if honorary, woman. The woman saw the dirty rug, and without being ordered to, cleaned it.

Well, maybe that’s not how she felt. But anyway, we are now close and easy. She lost a beloved older brother but gained a close sister. A paradox. Am I her older sister, or in fact much younger? Ha, ha.

* * *

How does a new gender feel after all these years?

Great.

Most decisions leave at least a small regret, a 4:00 a.m. wakefulness. Did you marry the right person? (In my case, yes.) Did you choose the right profession? (In my case, yes.) Should Donald have stayed at his beloved University of Chicago, which in 1980 he left from irritation at the reluctance in the Economics Department, though not in History, to promote him right away to full professor? (A hard one, that; but on the whole, yes.) But becoming Deirdre has evoked not the slightest passing instant of regret. Not once. Nada.

It’s about feeling comfortable in your own skin, as we say, not pleasure. But there are pleasures, certainly. I spoke in Crossing of the friendship of women and named some of them, but there have been many more since.

Women do cooperate. (So do men, but in a different way.) My women’s group at Grace Place Church has been supportive, and I to them. All for one and one for all, you might say. Listening, sharing our lives, an encouragement here, a fun movie outing there, a sensitive inquiry as to how things are going, help with the housework when you fall into a depression, a long road trip to southern Indiana praying and singing around a campfire at night. Michael, row the boat ashore. Amazing grace.

A lesbian colleague in economic history invited me a couple of times to her house in Evanston to what I learned was a big annual event among American lesbians—the Super Bowl. About fifteen women gathered on the big night, but only one of the women and I bothered to look at the game. I noted trap blocks on the line, and discussed them with the lone football fan. But even she and I were not all that interested in it. We all brought a covered dish. Most of the evening was spent in deep talk. Not about football. On the other hand, I remembered a little party I had had for women friends in Iowa City during my last year there to watch the women’s American soccer team defeat the Chinese in the World Cup. Still some deep talk and covered dishes, but we watched the game, too. The heck with the game. It was the friendship of women that mattered, to me and to them.

One December I went back to Australia, giving talks to thin gatherings of academics in the middle of their summer vacation, in cities that just happened each time to have the English touring team playing the Australians for the cricket prize known as The Ashes. Cricket is the only sporting passion left over from Donald. In Adelaide I stayed with an economist friend and his second, American wife. The husband and I would march off to watch the cricket every day, and she would pack lunches for us and send us off as though we were going down the pit to mine coal. So far as the fortunes of the English team that year was concerned, it might as well have been down the pit. On the last day, an hour before he was to take me to the airport, she said, “In a back closet I have some clothes I never wear. Do you want to try them?” Do birds fly? For an hour we rummaged through the closet, and I got outfits galore, two business suits, several tops, and on and on. They arrived by mail in Chicago a couple of months later. I’ve bought few clothes since then. The grace of women.

On another trip to what the Australians themselves call “Oz” (from “Aus-“) I gave a gender talk at Sydney University, and there in the audience was sweet Kate Cummings. I went the next day up the coast on the train, and Kate met me at the little station near her new home with her girlfriend, and we had a jolly time. Kate had showed me in 1995 that a professional could Do It, she being an academic librarian. A couple of years later I went to New York City, staying in Kate’s loving daughter’s tiny Manhattan apartment, to see the opening night of a new play about crossdressers at a resort back in the 1950s. Kate, expert in such matters, had advised the playwright. We got to go backstage to praise the actors.

Delight. Pleasure. But identity on the women’s team.

* * *

Have you had romance?

No.

Is it about sex? No.

Do you care?

No.

When I moved from Iowa City to Chicago in 2000 I decided to do some video dating. I was not sexually attracted to women any more. Try men, I thought. Maybe some Big Joop will come along. Truth to tell, my surgery had left me without physical sexual feelings, which was no loss. It’s a relief, actually, to stop the biological yearning. But it seemed appropriate and interesting, so I signed up with a respectable service downtown in Chicago, at which you made a video of yourself and the men chose you, like one of those hideous mixer dances we used to have at Harvard with Wellesley in the 1960s. I leveled with the consultant, but she saw nothing wrong with keeping The Secret, at least on the video itself.

So I had some dates. One was with a guy who drove me to dinner in his Cadillac and spent the whole evening talking, talking, about (1.) his dead wife and (2.) his business. He didn’t ask me anything. Not a word. Any woman here had that experience? He drove me back to my building, parked the car and waited for me to invite him up for, well, you know, we’re all adults here. But I’m an old fashioned girl, and said thank you for a lovely evening. Not. And scurried out of his car.

I had another date, with a guy who played the ponies, and I fantasized about becoming the girlfriend of a race-track man. I could do that. Another was a life coach. As soon as we met for lunch across the street from my place I could tell he didn’t warm to me, though he was insightful and intelligent, as one might expect from his job. My problem was that I always told the men the next day, and they never came back. The life coach replied to my email saying, “Oh, that’s why I didn’t find you attractive.” Well, thanks.

Finally I gave up. My girlfriends remind me that a tall, successful professional woman of a certain age will find it hard to get dates. Basically, impossible. Men are such dopes. Even without mention of The Other Matter. Join the crowd, dearie. I vaguely hoped that someone who Already Knew would fall for me, but it never happened. I had people living with me frequently, because my loft is large and it seems only Christian (or Muslim or Hindu) to share it with people having a hard time, and with a stream of out-of-town visitors. It’s nice to have a full house. I’m not lonely. But no romance.

* * *

Whacky and touching experiences abound.

In 2018 I gave to an enthusiastic audience including a cousin of mine a talk on, of all subjects, transsexuality and . . . economics at, of all places. . . the Central Intelligence Agency. If a transgender spy was threatened by the Russians with revealing her former gender, I suppose she would reply, “Feel free, fellas.” No blackmail would be possible, no Putin puppies.

At my 35th Harvard College reunion, in 1999, the first one I attended as Deirdre, my classmates had been genial. A man who ran a big fish wholesaling firm in Boston and who had played on the football team I captained in high school gave me a kiss on the cheek. At a contra-dance on the Radcliffe quad I partnered for a couple of hours with a shy, tall classmate whom I hadn’t known. The dance was elegant and fun, reminding me of square dancing with my wife in England and Sweden. I thanked the fellow afterwards, and he replied, by way of explaining why he didn’t recognize me from college, “I didn’t know many Radcliffe women.” I unthinkingly replied, “Well, neither did I.” Whoops. He looked at me strangely, but didn’t get it. At my 50th reunion in 2014 the Radcliffe women of my class invited me to join them in the big photo on the steps of Widener Library. Lovely! Only one woman, with whom I had thought I was having an affair in the spring of my freshman year, objected.

During the late 1990s shortly after my transition I had called up a male dean at Harvard and asked him if Harvard could change my degree to the women’s college, Radcliffe. “Oh, I don’t think we can do that.” “But the U. S. State Department,” I whined, “had no trouble changing my passport from male to female.” Pause. Then with a smile in his voice, “Yes. But Harvard is older than the U.S. Department of State.” Goodness. Some things never change.

When I gave a short talk to that 50th reunion I had meant to include the story as the punch line. It would have brought down the house. But my speaking technique, to avoid stuttering, is to simply stand and deliver, so I forgot. My classmates and spouses seemed to like the talk anyway. As I rolled my suitcase out of Adams House on the last day, a classmate I hadn’t known passed me, and a little down the street he turned and hailed, “Deirdre, we love you.” Sweet man. Sweet, tangled life of work and love, experienced and missed.

* * *

There’s a politics to it. We Americans live in a free country, as we like to affirm. Still, unlike, say, British or Dutch people, many Americans get really, really irritated when another American exercises her freedom. It’s an old tension in American life.

Gender change I reckon is a freedom thing, one of a long line of liberations from 1776 on. My writings are increasingly focused on the slow decline since then of the privileged classes, who get irritated or worse by the actions of the non-privileged. In 1776 John Adams, who was no democrat, worried about opening the Pandora’s box of, as the historian Alan Taylor put it, “promising equal rights in an unequal society”: “There will be no end of it. New claims will arise. Women will demand a vote. Lads from 12 to 21 will think their rights not enough attended to, and every man who has not a farthing will demand an equal voice.” He was right. The box could not be closed.

I’ve claimed in long books from the University of Chicago Press (2006, 2010, 2018, cheap on Amazon) that a change in ideology came over northwestern Europe in the 1700s and made the modern world, entire. Thus in America and slowly worldwide, 1800 to the present, a new liberalism gradually liberated poor white men, American Patriots (not Loyalists), Catholics, slaves, women, Irish, Jews, hillbillies, subjects of fascist tyrannies, colonized peoples, former slaves (again), women (again), other immigrants, gays, handicapped, subjects of socialist tyrannies, Chicanos, native Americans, East Asians, and, amazingly, transgender people. More and more people were allowed to have a go. The result was a fantastic flowering of creativity, from jazz to Steve Jobs, from the novel to Huffington.

Liberty made us rich and made us pretty good, too. People will say that slavery and Indian removal and worker exploitation also made us rich. No, they didn’t. You’re mistaken. Feel guilty about the evils, but do not think they were contributions to riches. I am an American humane libertarian—what is called elsewhere a “liberal” in the style of Adam Smith or Mary Wollstonecraft or Henry David Thoreau. I join, and I hope you do, with the African-American poet Langston Hughes, singing in 1935: “O, let America be America again — / The land that never has been yet / —And yet must be—the land where every man is free.”

And every woman, dear.

This article was edited after publication to remove a reference to the Birthday Paradox.

Deirdre N. McCloskey is is the Distinguished Professor of Economics, History, English, and Communication at the University of Illinois at Chicago (UIC). She is best known for her Bourgeois trilogy: The Bourgeois Virtues: Ethics for an Age of Commerce, Bourgeois Dignity: Why Economics Can’t Explain the Modern World, and Bourgeois Equality: How Ideas, Not Capital or Institutions, Enriched the World. This is the Afterword to the 20th anniversary edition of Crossing: A Memoir, now called Crossing: A Transgender Memoir, with a new Afterword.

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