Case Study

Questions of Gender

A therapist struggles with the clinical choices he’s made

Magazine Issue
September/October 2014
Questions of Gender

Sometimes I’ve been instrumental in helping couples stay married when perhaps they’d have been happier if they’d gotten divorced. Other times, it’s been the reverse. Obviously, we all know that’s it not our job to tell our clients what’s right for them: rather, we need to create the right conditions for them to discover the answers for themselves. Frequently, however, our own reactivity shapes the messages we send and how profoundly we can influence—in unconscious and unpredictable ways—the unfolding of some couples’ lives. I feel that way about my work with Glen and Julie over a 14-year span.

An Ordinary Case

Up until my eighth session with Julie and Glen, they’d seemed to be a vanilla kind of case—a middle-aged couple with two middle-school children, two careers, busy lives, and what seemed to me a pretty sweet relationship. They came to see me because they were having a painfully mediocre intimate life: she wasn’t all that interested in sex, and he felt hurt by always being in the initiating role, with little success. For her part, Julie was gently accepting of his difficulties with premature ejaculation and seemed perhaps too willing to be the problem. In their shared sense of fragility, they were usually extra careful not to hurt each other’s feelings. Then, toward the beginning of one session, Julie dropped a bomb.

“Well, I don’t think his ‘male needs,’ as you call them, Dr. Treadway, always get expressed so normally,” she announced. “A few years ago, I walked in on him dressed up in my underwear!”

“Damn it, Julie!” Glen yelled. “I can’t believe you brought that up here. So it’s all my fault now?”

I was stunned. I hadn’t seen this coming at all. Suddenly, we weren’t in Kansas anymore.

“So, Glen, it seems like you’re really hurt and shocked that Julie would bring this moment up in our therapy without warning,” I said.

“Damn straight. She always blamed everything on me anyway. I’ve never been good enough for her.”

“I’m sorry,” Julie said to Glen. “It’s just that I haven’t ever gotten that out of my head. We’ve never talked about it at home, either. I didn’t mean to bring it up, but it felt like you were making our sex problems all my fault. I’m so sorry.” She was now awash in tears.

“Well, it’s a little hard to take back now, isn’t it?” Glen said, still angry but with tears in his eyes.

I tried to be a comfort to each of them, normalizing how embarrassing secrets can sometimes be blurted out in the supposed safety of the therapy room and taking the blame for seeming to align too much with Glen’s sexual complaints. Meanwhile, the couple huddled in their separate corners of the sofa without looking at each other. They endured the rest of the hour and got out of there as fast as they could—without making another appointment.

I tried to reassure myself with my oft-repeated lines “more will be revealed” and “it’s not really about you.” But in reality, this was the first time in my practice that a cross-dressing situation had come up, and I was taken aback. In the following weeks, they didn’t return my phone messages, and I felt as if I’d blown the case. But after a month and half, I was delighted when they phoned to set up another appointment.

To my surprise, they shyly walked into my office holding hands. Julie asked Glen, “Do you want to tell him or shall I?”

“Why don’t you tell him,” he said with a little blush.

“Well, after that dreadful session, we finally talked about what came up. And then all of a sudden, he told me that it all started when his mom died, when he was 10. He told me that he used to go into her closet just to smell her smells because he missed her so much. One day, he was looking through her drawers and came across her lingerie, and the next thing . . . .” She paused and looked over at Glen. “Is it really okay if I say all this?”

He nodded without looking up.

“Well,” she continued, “he told me that’s a private activity he’s never told anyone about his whole life, and he was so ashamed when I walked in on him. And then he started to cry, and I was holding him, and then we were suddenly starting to, you know, get aroused. And then I offered to let him wear my underwear.”

“Okay, that’s enough,” Glen whispered quickly. “We don’t need to go into the specifics. He gets the drift.”

In the weeks that followed, I tried to support their newfound intimacy. Somehow, his vulnerability around his idiosyncratic way of feeling connected to his mother and Julie’s compassion for him had led to a rekindling of not only their sexual life, but also of their emotional connection.

Careful not to rock the boat as I had before, I was reluctant to probe deeply into his feelings about his cross-dressing or treat it as a psychological issue. After all, they seemed comfortable with his wearing her underwear as part of their sexual play, and it seemed to make them both feel more connected. I know other therapists might have more aggressively explored his attachment to wearing women’s lingerie, but I chose not to. It felt so right between them that I decided to let it be. They left therapy seemingly quite content, and I felt pleased about what felt like a happy ending.

Act Two

Eleven years later, Julie surprised me with a phone call. “A lot has changed,” she said in a way that sounded sad but didn’t prepare me for our session. So I was surprised when two women came into my office: Julie—looking wan and much older—and Glen—dressed fashionably as a woman with startlingly feminine features. It turned out that Glen, who was now referring to himself as Emily, had gotten electrolysis and was on female hormones. He, now she, was planning on completing her transition with implants and genital surgery.

“We’ve tried for a long time,” Julie said. “I so wanted to keep our family together, and it seemed like each step he made was somehow going to be the last step.” She started to tear up. “He’s been so preoccupied with feminizing himself and actually separating more from me. When I asked him to come back to see you, he said you didn’t know anything about trans issues. He insisted that we see a gender specialist who’d understand better, and I was willing to try anything. The therapist seemed to think this all was a natural evolution for Glen and that it didn’t mean he didn’t love me. But now Glen wants to go all the way, and I just can’t do that. I don’t want to be married to a woman, but he says he’s just not a man anymore.”

Glen/Emily began to cry and reach for tissues, and then in a low, soft, voice said, “I still love her. I still want to be with her forever. I never planned on this. Back when this all came out, we thought it was pretty harmless. Maybe we should have worked harder on it all then. Maybe I could have turned back. I know it sounds silly, but one thing just kept leading to another. And here I am. I want to just be me. And I want us to stay together. I know there are plenty of couples that find a way of staying together.”

After that, we had several sessions with many tears, but no movement. I tried challenging them to find some viable, mutually acceptable compromise, but Emily decided to complete her sex-change treatments, and Julie simply couldn’t continue down the path with her. They chose divorce.

Act Three

Three years later, Emily—now fully a woman—called for a session because she was distraught that her daughter had cut off all communication with her. She told me briefly over the phone that she and Julie had managed a careful and relatively friendly divorce, and their kids (Jack, now 23, and Sarah, now 21) seemed to be at peace with their decision. But since she’d started dating men, her relationship with Sarah had become estranged.

So, again, I saw Emily and Julie, this time about their parenting situation with Sarah. Although Julie and Emily were cordial, they weren’t close. They did still want to parent well together, and they both thought Sarah needed help dealing with Emily. Together, we agreed that I’d see Emily and Sarah in the next session together. Julie’s part would be persuading Sarah to come for the sake of the whole family.

Sarah slouched into the session as if she were an early adolescent. She was dressed in a disheveled manner, but Emily was impeccably put together, with pink lipstick and matching pink fingernails. I could barely see a trace of Glen.

After my usual efforts at joining, which fell pretty flat, I asked Sarah to describe growing up with her father.

She started to weep. “I loved my dad. He was funny and sweet and helped me with math and played my kind of games with me—like we could play house together better than mom could.” A shadow of a smile crossed her face. “And when I found out about the cross dressing,” she went on, “I handled it okay. It was gross, but mom seemed to be doing okay, and Jack put up with ‘Dad’s thing’ all right. Even after the divorce, he was still Dad. But now that Dad’s dating men, I don’t know what to do. Emily’s killed my dad. He’s gone. I don’t even know Emily. She’s not another mom, and she’s not Dad. Who’s supposed to walk me down the aisle?”

As Sarah curled up in a ball crying, there was silence. I nodded encouragingly to Emily.

Emily was daubing her eyes and then twisting the tissues in her lap. Finally, she said, “Sweetie, I’m so sorry. I will always be your dad, now and forever. I think I was so driven to become myself, and the family seemed so understanding, that I didn’t appreciate how hard this was for all of you. And you, in particular. You were always my little girl, and I know nothing can ever be the same again. I’m so sorry.”

Sarah looked at Emily for the first time. Emily put out her hand, and Sarah took it. Sarah didn’t want to come back for more sessions, but she did agree to have regular phone contacts and an occasional lunch with Emily. Emily was disappointed, but I thought Sarah was doing the best she could.


It’s been years since I’ve seen this family. While I was writing up this case, I decided to give Julie and Emily a call to see how they were doing. Julie, her marriage having ended and her kids having grown up, seemed sad and a little stuck. She wasn’t dating or working, but she did say that she and Emily were getting along tolerably well. They could do some family events together, though she was uncomfortable with including Emily’s partner. Emily, in contrast, seemed quite content and had found a male partner with whom she’d been living for the past couple years. Sarah, Emily said, was still standoffish, didn’t visit Emily’s home, and refused to meet her partner. But Sarah did keep up her agreement to see Emily from time to time and occasionally talk on the phone.

Was Emily’s transgender journey inevitable? Certainly some cross-dressing men stay within marriages and don’t feel compelled to live full-time as women or become women. In our early sessions, did my delicacy about not making Glen feel ashamed about his cross-dressing inadvertently undermine the couple’s ability to find a way of working through this together? Perhaps if I’d dug into the issue more, they’d have felt more comfortable coming back to me earlier to find some kind of compromise—something that didn’t seem to be part of the gender therapist’s agenda.

In retrospect, I realize how much my own uncertainty and conflict avoidance had made me tiptoe around the central issue in this case. I was reluctant to confront Emily about the effects her decision might have not only on her marriage, but also on her children. And I was hesitant to push Julie to consider joining a support group of wives, or even to explore her reluctance to consider making a life with a transgender husband, as other women have done. Somehow, their choice to see a transgender specialist, rather than come back to work with me, had frozen me in more uncertainty. I didn’t know much about cross-dressers or transgender individuals. Nor did I do what I tell my students to do all the time: seek supervision. I didn’t even consult with a gender specialist or call the one they’d been seeing. Was I too embarrassed about my choices throughout the case to ask for help? Or was I, in fact, unwilling to deal with the specialist because she sounded like too much of a trans advocate? More conflict avoidance?

I look back on my 14 off-and-on years with them with awe about their journey and doubt about my choices. Questions about whether this was a successful outcome and whether I should have done something differently still linger. Emily does seem to be confident in her journey, and the evolution of her sexual orientation implies that perhaps there never was a chance for her and Julie to stay together. But I’ve learned enough to know that complete transitions and divorce are not necessarily the only outcome for couples that face gender identity and/or orientation issues. Professor Jennifer Boylan, author of She’s Not There, chose to become a woman, and yet she and her wife managed to stay married and raise their children. And certainly, Julie and Sarah seem significantly less comfortable with the outcome of this story.

I’m still troubled by my difficulty in challenging them more at critical moments. The original session, in which I felt so badly about inadvertently precipitating a crisis with this couple, seemed to have constricted me in my work with them at critical moments during the ensuing years. They truly loved each other, and yet my diffidence around challenging them may have been the reason they didn’t stay in therapy with me and work to stay in the marriage. And it’s obvious in retrospect that I should have consulted early on with a trans specialist and sought supervision for myself.

How do any of us therapists know what’s “good enough” in the unfolding of people’s lives? Who knows what would have happened in this family if they’d tried to stay together? Perhaps it’s my hubris that makes me think that if I’d only done X, Y, or Z, then they’d have lived happily together ever after.

I know I practice an often intuitive craft, not an exact and predictable science. I bring my therapeutic models, repertoire of techniques, previous clinical experience, and all-too-limited personality to my encounter with the clients I see. And the truth is that all too often, like most practitioners, I can never be quite sure how much difference my bit part plays in the unfolding drama of their lives.

Case Commentary

By Jean Malpas

David Treadway’s candid reflections are refreshing and allow us to ponder the cases that take us outside our familiar field of vision. In this case, Treadway finds himself in foreign territory when Julie outs Glen’s cross-dressing behavior and the pink gender elephant emerges in the middle of the therapy room. At the end of act one, however, I wonder how the couple would have responded to a more specific, yet gentle, invitation to inquire further into the gender territory in individual sessions. For example, Treadway could have said, “I appreciate your willingness to return and discuss how you’re dealing with Glen’s desire to cross-dress. Many couples wouldn’t. I also know that many spouses would be disoriented by this discovery and would wonder how to understand it and integrate it into their lives. I sense that it’s still a delicate subject. I want to respect that and wonder whether it might be a good for us to meet separately, just a couple of times, and explore your respective feelings on this. While the individual meetings are confidential, we’d make sure to bring the helpful parts of our conversations to the next couple session.”

The privacy of the individual session would have allowed Glen to feel reassured about the therapist’s nonpathologizing perspective on gender fluidity and also given him the opportunity to assess whether he was a cisgender man—a person whose biological sex and gender identity are congruent with one another—with an erotic preference for cross-dressing play, or whether the behavior was anchored more deeply in a desire to actualize her core femininity. For Julie, the individual session could have allowed her to feel supported in her shock and grief and given her the opportunity to assess her willingness to transition along with Glen, if indeed he was transgender.

Nonetheless, the situation has clarified itself by act two: Glen has transitioned to Emily. Many couples, like Julie and Emily, are unable or unwilling to transcend such an important shift. But the therapeutic support Treadway offered here matters and can facilitate a more constructive separation. Generally, even the couples willing to work on transitioning together experience a deep crisis and question the foundations of their relationship. They may wonder, Are we still the same couple, or is everything different? Have we been fooling each other all along, or can we keep our life together? A therapeutic process more focused on gender would entail a complex and nonlinear exploration of grief, conflict, sexuality, and larger family relationships. In terms of grief, a sense of loss of the spouse and of the couple as they once were is common. Conflict is often exacerbated by the spouse’s feeling of being trapped in a marriage he or she didn’t sign up for. The partners have to shift from being victims of circumstances to exploring whether they can choose a new beginning together. In terms of sexuality, many questions need attention. Can the couple integrate cross-dressing in their sexual play? If the transgender spouse transitions physically, would the spouse still feel a sexual attraction, and vice versa? And finally, how would the couple deal with the process of coming out and renegotiating the terms of family and social relationships?

The family transition is exactly what David strives to facilitate in act three. His ability to be both affirming of Emily and empathic with Sarah lets Sarah voice her own grief about her father’s new reality. I remain curious, however, about the meaning that Emily’s choice of dating men holds for Sarah, and wonder what that exploration would have yielded. Why is Emily’ choice of men, more than her gender transition, a deal breaker in Sarah’s ability to relate to her father? Did Sarah believe that her parents’ marriage had been a sham all along? Did Emily’s sexuality make things too real? What would she have needed to grieve her father?

Treadway’s postscript reflections raise interesting questions about the meaning of success in therapy. Do we define it only by keeping couples together? Or can we consider the fact that this family used Treadway’s resources at every crucial turning point of their lives as a measure of success? After all, he did manage to create an environment both affirmative of Emily’s identity and attuned to the complex emotions of everyone in the family. I wouldn’t be surprised if the family returned in the future, and I look forward to act four.

Author’s Response

Thank you for the long overdue consultation on this tender case. Yes, retrospectively, I absolutely should’ve created some private space for the couple. Perhaps that would’ve made room for the possibility that there was already more complexity to Glen/Emily’s cross-dressing than it appeared, and we could’ve worked together to better understand it. Instead, I was too concerned with protecting this couple’s newly rejuvenated intimacy. If I’d done those individual sessions, they may have been able to do the work with me rather than going elsewhere.

Also, in regard to your thoughtful questions about why Sarah’s reactivity was focused on Emily dating men, she said that it forced her to really deal with her father having become a woman. It felt to her like a “straw that breaks the camel’s back” moment. Although she was reluctant to work on it, I actually think she was expressing loyalty to her mother and perhaps, unconsciously, feeling her own femininity being rejected, in addition to her grief about losing her dad.


Illustration © Sally Wern Comport

David Treadway

David Treadway, PhD, is a therapist and trainer of 40 years.  His latest book is Treating Couples Well: A Practical Guide to Collaborative Couple Therapy. He’s also the author of Home Before Dark: A Family Portrait of Cancer and three other books.

Jean Malpas

Jean Malpas, LMFT, LMHC, is the director of the Gender & Family Project and director of international training at the Ackerman Institute for the Family. He maintains a private practice in New York City. Visit his website.