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Couch is a series about psychotherapy.

“So who is that dowdy person that always comes at lunchtime?” my officemate asked.

I knew immediately whom he was referring to: Greta, a woman in her 30s who faithfully took her seat in the waiting room at midday every Wednesday and sat stiffly until I opened my office door. With her homely dresses and unstylish hairdo, Greta looked like someone you’d see in a 1950s Good Housekeeping magazine.

“She’s great,” I said. “A really interesting person.”

This was true, but my officemate was right: Greta was not exactly alluring. It wasn’t her looks, which were fine (I’m certainly no Adonis myself); it was her unfashionable dress and grooming. Which was a shame, not because I cared how she looked, but because Greta herself so deeply yearned for a romantic relationship.

A boyfriend, then marriage, and soon after that, kids — that was pretty much all that Greta felt was missing from her otherwise enviable existence, which included Ivy League degrees, a Wall Street career, a downtown loft. There was a lot of back story: She had overcome a difficult upbringing in a small Midwestern town; her mother had died young; her father was strict and domineering. And so on. All of which made her accomplishments that much more impressive.

For more than a year, Greta and I met once and sometimes twice per week for psychotherapy and medication treatment. She suffered from panic attacks, which we found responded to low doses of Klonopin and Lexapro. In therapy, we addressed the frustrations of her office politics, her conflicts with her brothers, her mixture of sadness and relief when her father died. And she got better: She became calmer and more assertive, and formed stronger friendships. Her career thrived.

The only area of her life that didn’t improve was romance. Not that she didn’t go on dates, but they typically were one-off events. There never seemed to be a spark, much less a flame.

One day, after a bit of hemming and hawing — I knew it would be a sensitive topic — I raised the obvious: Had she considered getting a makeover? One of her friends, as Greta herself had told me, had recently seen an “image consultant” who recommended a whole new wardrobe, new hairstyle, different makeup. Could that, I asked, possibly be helpful?

“After all,” I added, “men tend to judge … ”

Greta bristled, and I stopped midsentence.

“You know,” she said, “I look much better when I go on a date. I put on makeup, I dress up. My friends say I look great!”

That shut me up.

For a number of months — in retrospect, far too long — I accepted that explanation. Her friends no doubt were attuned to the actual workings of the dating world, whereas as a married man, I’d been off the market for years. What did I know?

Over time, though, I began to wonder. I couldn’t really imagine that Greta underwent a major transformation on weekends. Plus, her dowdy persona Monday through Friday couldn’t help but decrease the odds of a fortuitous encounter with a future romantic partner during the week.

I’ll be the first to say that looks shouldn’t matter, that we shouldn’t judge people based on superficial criteria. But it’s also true that there are costs to ignoring, or defying, the social realities of the world we live in, and I suspected that Greta was paying those costs.

By objecting so strenuously to my makeover idea, Greta gave me an easy out. She clearly didn’t want to touch that issue. It was her treatment; she was choosing what to focus on. So I let it go. For years.

The real problem was that I didn’t know what to do in this situation. Years of psychotherapy training had given me no guidance in how to deal with the staunchly dowdy patient. Starting early in our training, we psychiatry residents spent innumerable hours addressing issues raised by inappropriately seductive patients. How best to deal with patients who flirt in session, who wear inappropriate attire, who ignore boundaries, who try, whether consciously or not, to lure you away from “therapeutic neutrality”? There were articles, books and lectures that helped us deal with a patient’s “erotic transference” and our own “countertransference reactions.”

But advice about the patient who refuses to be attractive? No.

Maybe a female or gay male therapist would have had an easier time addressing this topic with Greta. But for me, as a straight male working with a straight female patient, every option seemed blocked. Basically, no matter how I tried to put it, I would be saying, “I find you unappealing.”

Which, at least to Greta, would have raised the reasonable question, Why on earth would she want me to find her appealing? The whole thing reeked of grossness. Like it or not, in raising the issue, I could be viewed as endorsing regressive cultural norms, implicitly justifying or defending the regrettable behavior of my gender.

When I eventually tried again to discuss the issue of her appearance, things did indeed play out this way. Greta began to find me slightly creepy. Since previous therapists had never brought up this topic with her, she came to the conclusion that there must be something wrong with me for mentioning it. I don’t think she was right, but I can understand why she thought so.

This story does not end well. After nearly a decade of our work together, Greta remained unhappily single. When she was offered a job transfer to California, she took it and moved away. We did some telephone sessions and I continued to renew her medications until she found a new doctor. And that was it.

Last year, after a long hiatus, Greta came back to town. She made an appointment with me for a review of her medications, which she’d been getting from her primary care doctor and which had become less effective. I felt a bit of anticipation, perhaps hoping that she had been transformed with the help of a new therapist or the mellowing effects of California culture.

Related More From Couch Read previous contributions to this series.

Alas, when she came for her appointment, it was clear that little had changed. Greta looked the same: the same Good Housekeeping hair, the same frumpy skirt and too-sensible shoes.

And her life? She filled me in: Her career was fine, she had a circle of new friends. But in terms of relationships? Nothing. After our work together, she had concluded that she just wasn’t meant to have romance. She had resigned herself to solitude.

Every therapist at some point discovers his limitations, be it a type of person he can’t help or an issue he is unable to successfully address. For whatever reason — a poor match of patient and doctor? my own deficiencies as a therapist? the complexities of our society’s gender relations? — the dowdy patient was mine.­

Details have been altered to protect patient privacy.

David J. Hellerstein, a professor of clinical psychiatry at the Columbia University College of Physicians and Surgeons, is the author of “Heal Your Brain: How the New Neuropsychiatry Can Help You Go From Better to Well.”