Illustration by Dave van Patten

Why Men Have So Much Trouble Getting Over ‘The One Who Got Away’

The first time Mark Elderfield thought he let “the one” get away was when he was 17 years old. Her name was Caitlin*, and she was his first love. But he was a young, “dumb fucker” who wasn’t emotionally mature enough yet for a real relationship. He cheated on her, and the relationship ended after two years.

“You know that first person who takes an interest in you?” asks Elderfield, a 46-year-old therapist in Galway, Ireland. “The absolute infatuation you have with them? She was the first person who liked me. I’m not even sure I knew what love was.”

Looking back, it wasn’t a whirlwind romance. “I can’t see any sonnets being written about it,” he says. But the second it was over, he was sure he had lost the love of his life, and no one would ever replace her. It took another 18 months before he could see her without his stomach twisting into knots, he says, and another two decades before he was completely over her. Even at the age of 38, he secretly harbored thoughts that they would get back together, and his feelings would be vindicated.

The main characters in the 2010 bro comedy Hot Tub Time Machine call their respective lost loves The Great White Buffalo. My college friends and I referred to ours as our White Whale, a reference to Captain Ahab and his undying, self-destructive obsession with his literal white whale, Moby Dick.

Most men, though, just call her the The One Who Got Away.

While a 2015 Binghamton University study found that breakups take a larger emotional toll on women — reinforcing the stereotypical image of a woman rendered hysterical by her relationship dissolving — it also found that men generally take longer to get over a relationship, lending credence to the perpetually lovelorn male archetype we so often see in pop culture — the pensive, 30-something man who’s still hung up on his high school sweetheart. (See: There’s Something About Mary and Grosse Pointe Blank.)

Santa Fe native Joseph Uranga, 21, met his One Who Got Away in junior high on MySpace. After three months of internet correspondence, they met IRL at the mall and kissed. “It was exhilarating. I was on top of the world, ya know?” he says.

They dated for 10 months — hanging out at the mall, going to the park, seeing movies — until Uranga abruptly broke up with her one night over the phone. He was frustrated they couldn’t spend more time together. “If I wouldn’t have been so foolish and young, I’m pretty sure I’d still be with her to this day,” he says.

He’s dated other women since, but none have measured up to his junior high girlfriend. He occasionally peeps his ex and her new boyfriend on social media, traveling the world together, and thinks, Maybe that could have been us.

Uranga says many of his friends have an ex they’re still in love with, too, and their coping mechanism is to just date other women. “Like, a lot of other women,” he says.

This is a typical reaction for men experiencing heartbreak, says Elderfield, who routinely holds group therapy sessions for men. (Hence the saying, “The best way to get over one woman is to get under another.”)

“Guys aren’t particularly well-equipped for handling emotional issues, so avoidance is typically the method,” he explains. And that avoidance allows their feelings for their ex to linger. “It just sits there in the background. … And everyone else you meet is going to have trouble living up to that unrealistic standard, because we tend to only remember the good parts of the relationship.”

Take, for instance, Andrew Walker, the 47-year-old COO of Prism Intelligence, a Seattle-based data analytics firm. He met his One Who Got Away when he was just in grade school. They were together in their school’s gifted program, and their friendship blossomed into “teenage puppy love” when they reached high school, he says.

But she was a year older than Walker, and he broke things off when she went away to college out of a mix of insecurity and jealousy. “I didn’t trust her. I incorrectly assumed that seniors in college had a lot more to offer her than seniors in high school. So I tanked [the relationship].”

Walker resigned to never loving another woman as much again, straying from one unfulfilling sexual relationship to the next until marrying in his mid-30s.

But Walker’s one who got away story has a rare, heart-warming ending.

He divorced his first wife eight years ago, at which point he serendipitously reconnected with his One Who Got Away on Facebook. He was looking for a developer for his burgeoning tech business, and she just so happened to be a software engineer. They became partners, and “in the process of rebuilding the company, we remembered who we were to each other.” They’ve been married five years now.

“If I were a non-rational person, I’d say it was cosmic intervention,” Walker says. “Had we reconnected any earlier, I don’t think it would’ve had the happy ending it did. It wasn’t until that particular moment that it was able to work.”

Walker says men obsess over their Ones Who Got Away for the same reason they can’t let go of their high school sports memories. “There’s an element of, ‘If I could play that last inning again, I’d win it this time,’” he says. Real-life relationships are “hard, they smell, they have sharp corners, they take a lot of work,” and can never compare to the romanticized version of life we keep in our heads.

That said, he urges men to try to track down their long-lost loves to tell them how they feel. “If they say, ‘You’re high. You were cute 20 years ago, but I don’t feel the same anymore,’ that sucks. But at least you’ll have tried.”

Or maybe you’ll end up marrying her.