Why Thinking About ‘The One that Got Away’ Is Ruining Your Relationships

The thought of what could have been is often more powerful than the memory of what actually was. Many of us have a “one that got away”—that perfect person we let slide through our fingers who becomes the yardstick by which we measure all our future relationships. One survey found that one in seven people in their 70s still pine for the one they let slip away; no matter how old we get, many of us still wonder about what could have been.

“I was studying abroad and there was this guy I had a crush on. We hooked up after a party and he wanted me to stay over, but I thought I would play it cool and went back to where I was staying,” says Allison*. “A few days later, I realized he was really hurt by that, and I tried to repair things, but the momentum was gone. He started dating someone else.”

Many years later, Allison still believes her semester abroad would have been more successful if everything had worked out with her crush. This kind of magical thinking is not unique, according Dr. Sarah Millstein, a clinical social worker and therapist located in New York, who has seen the thought process come up in her practice. “I believe it is not the reality of that person. The person has been turned into an object that represents things far beyond and likely unrelated to who that person is,” she tells Broadly. “What unconscious or imagined desired qualities can that ‘object’ bestow? There is a longing for perfection and wholeness that can be particularly intense when a person has a history of loss.”

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Fixating on the “one that got away” can become particularly terrible if it gets in the way of focusing on building a healthy relationship. “A healthy person is able to see all the qualities of the object and understand that he/she was not perfect—not ‘the only one,’” explains Millstein. But the fixation can become severe if people are unwilling, whether because of trauma or learned behavior, to see their fantasy object as a real person.

I was convinced I had made the biggest mistake of my life.

“I had an emotional affair with a man who was in a very serious relationship,” says Alaina. “At one point there was definitely an opportunity to make things physical. I never pursued it and when they got married I was convinced I had made the biggest mistake of my life. I sat in the back row of their wedding (without a date) and sobbed and had to pretend it was because I was happy for them, but really I was just miserable in every aspect of my life.”

Alaina, who has been in a relationship now for a year, sees how her obsession led to her unhappiness in other relationships. “I compared everyone to him,” she says. “But we’d never even kissed so I have no idea what it would have been like to date him in real life. In my head, everything was perfect.”

Millstein agrees that fixating on the idea of “the one that got away” is unhealthy, but stresses that it is something many people do and not just in the context of romantic relationships. “This is an interesting and complex topic and applies to so many things—the ‘best’ vacation, pair of shoes, etc. Everyone wants to win gold,” she says.

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Sometimes the overly simplistic nature of this kind of belief becomes obvious only when the situation is flipped. Alaina was recently contacted by a man she dated in college, which was more than a decade ago for her. “He asked me if I wanted to go on a trip with him,” she says. “It felt so random and out of the blue for me that it was kind of creepy. He couldn’t know who I was as a person all these years later.” It was only when she compared her own experience with the married man that she realized that, in this case, she was the “one that got away.”

*Names have been changed.