Leroy was an exceptional man. Except, for one reason or another, no one wanted to date him. It led to much confusion, then suffering. Why?
In answering this question, he began to consider his mother. The cause of his loneliness might be in her. Only, she was a grand woman, always available to him and to his other siblings. She maybe worked a few too many hours at the office, but other than that, she spent each free one evenly divided among her children. She was pretty, but not too pretty. And a wonderful role model.
She of course attracted a high school sweetheart, who would propose to her in an old fashion way. A week before their wedding, however, the groom passed due to a medical complication. Although brokenhearted, she never threw away the pieces of her heart. It wasn’t until after graduating with a major she was passionate about, and getting her first job in a field that thrilled her, that the mother ever fell in love again. Her second time was the last, with Leroy’s father. Now, he also makes for a great case study.
The father of Leroy was a good man, strong, free-willed, and caring. From the moment he lay eyes on who would become his wife, to his dying day, the father’s devotion was worth emulating. He wasn’t clingy. He wasn’t absent. Instead, the virtue he exercised was patience. The father managed to wait for the woman of his dreams to heal, for the mother of his children to open up.
Both grew to hold high positions in their respective companies. Together they could provide for a family twice their size. Family trips were common. Love abounded. And the biggest lessons the parents imparted on their children were what they themselves exemplified.
Leroy felt the path set before him and sought it with all the vigor a healthy youth could.
Honor roll in elementary, and middle school. B’s in high school. And a scholarship for athletics led him to compete for a championship league college swim team. Leroy had great lungs, and a great body. His grades were among the top of his class. And he graduated with a job at a respectable corporation. But still no luck with the ladies.
Leroy frustrated many girls throughout his grade school years. He was either too busy after school, or too shy to follow his friends’ leads. For prom he went with his cousin. No dinner, no limo, and after the dance, she went to her boyfriend’s house, as the two of them drank beers and smoked pot and laughed at memes the rest of the night. While poor Leroy, struggling to chug down his lemon vodka at the after-prom, felt terribly alone. No matter how many people surrounded him.
Into college, the demands made on him by his team and his studies, paired with the anonymity of a large college campus, made it to where he could be alone if he wanted. Of course he dated, though, eager to met the right person.
Freshman year he went on a few promising dates with Jackie. She was kind and tender, and very curvy. The minute Leroy considered taking her home for a weekend, he received a disconcerting message. Unfortunately, she wanted to get back with her ex. This setback hurt Leroy. And a year went by.
Sophomore year Leroy met Hannah. She put studies above all else, and was bent on maintaining her scholarship. Leroy went with her to the library every evening, to study. The day he suggested they go to his apartment after studying, she put it to him straight. She wasn’t in to him like that, or to any guy for that matter. Leroy took the hint and didn’t date for a few months.
Junior year, Leroy made his most promising connection. Her name was Doris. She loved to dance, to play, to sing, to live and breathe the arts. And was very affectionate outwardly toward Leroy, too. She took his virginity. It was beautiful.
Until one day a terrible accident took her life. Leroy sat at the hospital, not even feeling his own bandages, much less hers, until he let go of her hand. And then went home.
One day, on his way to his corporate job, he heard some self-help advice that changed his life. He quit his old life and decided to open his own canned food non-profit. It became incredibly successful. He devoted every waking hour to fundraising, marketing, procurement of foods, that the organization blossomed. He even recruited the right people, and pushed it even further, into a regional, then state-wide enterprise.
Around the time his hometown was holding an awards ceremony to celebrate him, it struck Leroy that he was alone, terribly alone, as he had always been. There was no one romantically in his life to share the win with.
Because of his reach and influence, Leroy felt he had the permission to enter into a few risqué affairs with secretaries, interns, neighbors, and politicians’ daughters. Of course none of these lasted, for they did not satisfy him at his core. What he wanted was something real, something he could share with the world, and someone who would share it with him.
Dating apps led nowhere. Friends of friends only got him so far. He was running out of ideas.
Around the time he had his first gray hairs, Leroy started traveling extensively. Previously, he would avoid it, or delegate the work travel to someone else. But now he craved it.
After a string of run ins with interesting members of the opposite sex at airport lounge restrooms and bedbug infested hostels, Leroy got hooked to the thrill of meeting complete strangers. There was Europa — clearly one of the many false names of the enchantress who rode camels with him, and rode him too, for six months through Sahara and Magreb — a mirage of a woman, one to only remember. Since, for one reason or another, she told Leroy as they crossed the strait of Gibralter that things would be over between them as soon as they reached her home country.
Was he really undatable? No. He had gone on dates. Was he not a catch? No, not that either. So what was it? What’s the thing that’s been missing this whole time?
Maybe, just maybe, he didn’t know what he wanted. Only, Leroy would have denied this, because he did want things, and he had gotten those things before. But now? What he wanted was to stay with a woman, to have children, and to provide for them until his dying day.
He could ask his parents for advice, but they wouldn’t say anything different than what they told him as he was growing up. Leroy considered that it was precisely their lessons that were holding him back. So he went instead to his three siblings for advice. The three of them were married by now.
The first sister told Leroy that what his problem was was that he gave off too strong an impression. Ease up, she told him. You intimidate people. So, despite his belief that he should always be himself and be proud of it, Leroy started caring a little more than what was habit about what others thought of him. This made working with him a lot more enjoyable, but still no luck in romantic relationships. One woman he went on a date with actually had the guts to tell him how boring he was to his face, when all he did was listen to her, all night.
So Leroy went to his second sister. She had different advice. She told Leroy that the problem was that he was too cavalier, too nice. What he should have done on that last date was thrown his french fries at that stupid ass girl, how dare she. So Leroy took his second sisters advice and went back to dating. Only now, more dangerously. Leroy found out just how easy it is to make a girl cry. Body image was effective, but cheap. Making them always pay was fun, but it didn’t lead to more dates, the way making fun of a girl does. He could insult their intelligence, habits, clothes, mannerisms, political beliefs, but in too short a time this led to resentment, and then to no more dates.
Eventually the charm of being an asshole wore off on Leroy, as he realized that being mean was just as alienating as being an undateable nice guy. And yet, at least being an asshole gave him the pleasure, the plausible explanation as to why girls left him in the end. At last, he had an excuse.
Years go by, and his non-profit fails. For good. He took up one job, then another, until landing at his old company again. It wasn’t so bad, only it sucked to not have someone to share his life with.
He could have gone to his oldest sibling for advice but he instead went to therapy. Paying for things makes them more real to some people. The therapist suggested some drugs for the pain, and some contextualization for his loneliness. Maybe he was after the wrong sex all along, therapist said.
Leroy took it to the T, and started going on not so reluctant dates with men. The expression, Don’t knock it till you try, took on a sort of irony when he realized he had to be knocked quite a bit before realizing it wasn’t his thing.
Disappointed, he went to his oldest brother, finally. Both had wrinkles, small ones, and gray chest hair.
The older brother and his wife welcomed Leroy into their home. After playing with the nieces and nephews a few hours, till the sun had long gone down, the blood relatives got to talking.
“Why am I alone?” asked Leroy.
“Because,” said the older brother, “I don’t know.”
“What can I do,” asked Leroy, desperate, shaking his hands. “I’ve tried everything, lived all over, started my own business, worked many jobs, dated non-stop, come from a good family, had an interesting life, am good looking, healthy, humble, funny when I have to be, empathetic, a bit of an asshole sometimes, perfect in other ways, yet not too ideal, still athletic for my age, from a good family . . .”
“You already said that.”
“What is it then? Why don’t women love me?”
“And you’ve tried men?”
“Men don’t stick around either.”
The older brother leaned back into his chair, the way you do when you are deep in contemplation. The brother knew Leroy’s story all too well, had heard it from the very beginning. So he was as blind as Leroy. Except for one thing. Their hot tea had turned cold before he spoke it: “Do you remember what mom and dad taught us?”
“Dude, it’s their fault I’m in this mess.”
The older brother looked skeptically at the younger.
Leroy retracted. “I’m not supposed to blame them, fine. What did they say?”
“Have heart. Be patient.”
“That’s it? Well, I already have a heart.”
“That just leaves you the one, then, doesn’t it?”
Decades go by. Leroy never marries. But he does have a few more interesting relationships. He writes a memoir, becomes a celebrity for a bit, and from it makes enough money to live comfortably until retirement, plus with his job which he has kept, and all the stories he has lived, he has more than enough reason to reach the end of his life.
Then he dies. And the world smiles. Because real life finds a way. It always does.