A beautiful woman’s observation just shook my old self-perception

By David McElroy · October 24, 2026

At some point — about 12 years ago — Amanda and I had exchanged phone numbers. That’s what she told me tonight, but I don’t remember it.

She worked at a restaurant in a part of town where I used to live. I had just bought the house where I live now, so I was about to move. We apparently exchanged numbers — the way people sometimes do when they say they’ll stay in touch — but I never called her.

Until she called me out of the blue Friday evening, I hadn’t thought about her for a very long time. If someone had asked me about her, I would have assumed she had forgotten all about me, too.

But Amanda has been troubled lately. And she said her thoughts kept coming back to a man who used to talk with her about her unhappiness and her dysfunctional family, especially her narcissistic father. I understood a lot about her because I was still coming to grips with my own narcissistic father and my own dysfunctional childhood.

We talked on the phone for a little while and then agreed to meet at a restaurant near my house about 9:30 p.m.

I thought I was meeting her just to be an amateur therapist and caring listener. For almost three hours, that’s what happened. But as we were in the parking lot saying our goodbyes, she said something that made me very uncomfortable.

Amanda said something about me that contradicted everything I believe about myself.

For any of this to make sense, I have to explain that Amanda was an aspiring model when I knew her. She was — and remains — drop-dead gorgeous. She has piercing green eyes and a perfect face. She’s tall and has a body that meets the model stereotypes.

She was beautiful when I knew her at the age of 22. She’s still beautiful 12 years later.

Amanda has been unhappy since I knew her. She’s had a series of unhappy relationships. Her modeling career never led to anything more than a bit of local work. She had continued to work at restaurants and had gone from one bad relationship to another. She had one brief and unhappy marriage.

But at the age of 34, she has little to show for herself. She has no family left. She doesn’t trust the men she’s allowed to take up her time. She never learned how to do much of anything except look beautiful and pose for cameras. And now she’s older than what that industry wants.

Amanda’s unhappy. She’s alone. And she is terrified that she’s wasted her life.

She was emotional and teary-eyed through parts of our conversation tonight. She told me that she was admitting things to me that she hadn’t been able to tell anyone else — things she had needed to say.

She told me that if she still had even one true friend in her life, she wouldn’t have reached out to me. She said she had a lot of acquaintances — shallow connections who had been good for parties and fun — but there was nobody she trusted.

The restaurant locked its doors at midnight and employees started cleaning up. They told us they didn’t mind us sticking around while they cleaned, but by 12:30, we had started to move toward our cars.

As we stood in the chilly night air — not sure what was left to say — Amanda got emotional once more. I was wrapping everything up and trying to give her a supportive send-off for the night.

I was telling her how much she had going for her — that she still had beauty and emotional depth and intelligence, even if she had never developed her skills.

She grew agitated and started crying again.

“That’s easy for you to say,” she said. “You’ve always been the one who everybody in every room looked at. You’ve always been the smartest guy in every room. You’ve always been the most charming man in every room. And you’ve always been the most good-looking and sophisticated guy in every room.

“Every man would want to be like you, but no woman would ever want to be like me.”

If I hadn’t realized how serious our conversation was, I would have thought she was playfully mocking me.

I’ve always felt like the smart guy, so there was nothing surprising about that. There are even times when I feel charming, so I could accept that, too.

But I’m not the good-looking or sophisticated guy. I grew up completely confident about many things about my skills and intelligence — but I also grew up with the absolute certainty that I was the ugliest boy God ever created.

I’ve never felt the least bit attractive. And now I was standing in a parking lot on a cold night listening to one of the most beautiful women I’ve ever known tell me that I was “good-looking and sophisticated.”

I jokingly tried to deflect what she was saying, simply because humor is the only way I know to deal with something that makes me as uncomfortable as her comments made me. But she doubled down on it.

Amanda is really down on herself right now, so I understand how she could undervalue herself. But it baffled me to find her pouring her heart out and explaining that I couldn’t possibly understand what it felt like to be so flawed — as she felt — because she had seen me as flawless.

As we finished saying our goodbyes, I turned the subject back to her, because she’s the one who was supposed to be the subject. Not me. So I didn’t try to explain how confused her words made me feel about myself.

But as I drove home, I couldn’t stop thinking about Amanda’s words.

I suppose if she were an unattractive woman — or even a moderately attractive woman — I wouldn’t be so confused by what she had said about me. But this is a woman who had moved in “model circles.” She was beautiful enough to attract any man she wanted.

To put it mildly, Amanda was — and remains — way out of my league.

And as I sit here thinking about it at 3 in the morning, I can’t help but wonder — yet again — whether my negative evaluations of myself stop me from getting some of the things I want in life.

I’ll never really be the best-looking and most sophisticated man in any room. Or if I am, it might be a room filled with very ugly and strange-looking men.

(See. Even now — as I’m trying to draw some sort of conclusion from this — I’m rushing to make fun of it in order to make the discomfort go away.)

But even if I never look like a model who’s fit to appear in the pages of GQ, maybe I’m not really the ugliest child God ever made. Maybe I’m not so unattractive that a woman would have to want me for my mind and my heart — and love me despite my looks.

That’s not something I’m yet emotionally prepared to accept, but I have a lot to think about.

Seeing myself through the eyes of one beautiful woman — at least briefly — makes me wonder what else about my self-perception doesn’t match reality through other people’s eyes.

Somehow, that’s terrifying.

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