Fiction: My Daughter’s Boyfriends

First Prize in Lilith’s 2020 Fiction Contest.


Jack is Naomi’s first boyfriend. They meet the first day in nursery school and are inseparable. He is a red-headed boy with freckles and mischievous green eyes. Jack also likes to wear Naomi’s dresses. A lot. Every time I arrive home from work, the babysitter says, “Jacqueline is wearing Naomi’s ballet tutu again.” Jacqueline is how Jack likes to be referred to during his play dates. His favorite outfit is a pink leotard and a  pink tutu Naomi won’t wear since she hates ballet class. He also favors Naomi’s Cinderella costume that her Grandmother brought her from Disneyland. Luckily Jack has not discovered my makeup cabinet. Since Jack just lives down the block, I usually drop him off at his apartment near Morningside Park. I am terrified that his father, a sergeant high up in the police force, could arrive at our apartment and discover him.

I am home from a too-long meeting with a magazine editor and my sitter is pale. “I didn’t know what to do,” she stammers. Jack’s father is standing at the doorway of my daughter’s bedroom. I slowly walk toward him and peek into the bedroom. Today Jack has chosen Naomi’s best party dress, which is a shocking pink velvet, with several beaded necklaces. If he wore a black bob, he would resemble a flapper from the 1920s. Jack’s father towers over me. He is still in his police sergeant’s uniform. I hold my breath as Jack’s father watches his son and Naomi jump up and down the bed.

“Hello,” I say nervously, but I am surprised. Jack’s father is laughing. Laughing so loudly that for a moment I think he is crying.

“Holy Mother of God,” Jack’s father exclaims. “Just look at him! Jack, you’re gorgeous. Absolutely gorgeous!”

And Jack’s father is right. His son is gorgeous.

Pedro is from Buenos Aires and has already enchanted the entire second grade. According to Naomi, she, Elisa Schwartz, and Rosie Marks all want to marry him. Pedro is such a sensation that the second-grade teacher, Mrs. Levy, has called an emergency parents’ meeting to discuss the discord that Pedro has brought into the classroom. It seems that the girls have been fighting over Pedro in the cafeteria, the gym, and the playground.

One would expect Pedro to be a mini Antonio Banderas, but he is just a soft-spoken little boy with long lashes and shiny brown hair, who is obsessed with turtles and doesn’t have the remotest interest in girls. Sobbing, Naomi is convinced that Pedro will marry Sylvia Cohen, who brings food for Pedro’s turtle. But her worries are for naught as Pedro’s family is suddenly being transferred to London. There isn’t even a going away party, but he does leave his pet turtle behind. The turtle is duly taken care of by every single girl in the class until the school custodian turns the heat off one night and the turtle, named Nueva York for Pedro’s brief home, dies from the cold.

Harlan is named after the famous science fiction writer Harlan Ellison; his father tells me this at our synagogue parents’ night. Harlan likes to read comic books and does not like to cut his hair, so it’s as long as the girls in Naomi’s Hebrew class. Harlan is madly in love with Naomi and brings her scary comics with violent covers of exploding things, which Naomi tolerates. She doesn’t really love Harlan, she tells me, but she will let him visit her and draw fantastic creatures in her notebooks. It helps that Harlan tells Naomi that she is beautiful about twenty times an hour. “Every girl needs to be told she is beautiful twenty times an hour,” I tell my husband, who as usual is not listening to me, but reading his most recent legal brief. One afternoon Harlan is too preoccupied to notice that he is crossing against a red light and is hit by a delivery bicycle. Thankfully, Harlan only suffers a broken leg, but his parents keep him home for his recuperation. Naomi doesn’t have time to visit him since she is currently obsessed with horses and spends hours in Central Park watching the riders gallop along the bridle path.

When Harlan finally recovers, he has fallen out of love with Naomi and in love with Jill Kleiner, the rabbi’s daughter. Naomi is miserable for two nights and then decides that Harlan was a nerd and develops a crush on Kevin Bacon while watching Footloose at her older cousin Rachel’s house.

Roger is Naomi’s first boyfriend who does not live in New York City. They met during an eighth grade dance at Naomi’s sleepaway camp in the Berkshires. Roger lives in Portland, Maine. “I didn’t know there are Jewish boys in Maine,” Naomi told me. They have long phone conversations in Naomi’s bedroom which has a large PRI VATE sign taped on the door. She is lucky she has no interfering siblings. I suspect that for the first time in his life my husband is jealous of a boy who is beginning to resemble a man. Roger has been left back a year in school and so technically should be going to high school. A photograph I discover hidden in Naomi’s desk shows a giant who actually needs a shave.

One night, Naomi discovers through her friend Sharon whose cousin who by some incredible coincidence attends the same Portland, Maine school as Roger that he is dating not one but three girls at the same time including a high school junior. The night that Naomi breaks up with him is also the night she has her first period. From then on, whenever she has menstrual cramps, she refers to them as “Roger’s Revenge.”

Josh is the killer. He is Naomi’s ninth-grade crush that lasts through the end of twelfth grade. Josh is devastatingly and dangerously handsome—a private school version of Jim Morrison who plays guitar in a band that does terrible covers of the rock songs that I listened to in the 1970s. No one cares about his lack of guitar skills or that he forgets the lyrics. If I were fourteen, I would be mad about Josh too. He is famous for being thrown out of every Hebrew school, and insisting on wearing a leather jacket during his bar mitzvah. Naomi’s love is the unrequited kind, the worst. I know that there are mornings she lingers on the street outside his apartment building. I hear her speaking about this to her friends on the phone and also about how she has made close friends with all of Josh’s doormen. Has Josh ever acknowledged her? I know from my own experiences with boys like Josh that he is too cool to notice anyone except himself. Eventually Josh’s parents will divorce and he will move with his mother to Asheville, North Carolina, which is too far for Naomi to follow. Yet he hovers still about her high school years like the weather—it is always there even though it changes.

Several years later, when Naomi is in college, I will find a torn napkin hidden deep in her desk with a scrawled phone number and Josh’s signature. Did he give this to Naomi or did Naomi find this and keep it to herself as a wish or a souvenir? All I can hope is that Josh at some moment in time was kind to her.

In 11th grade, Arthur can almost make Naomi forget Josh. He is the child of two Deadheads who are now doctors, and with his ponytail, vintage tie-dyed t-shirts, and John Lennon glasses could be from a different decade. Naomi, who has recently been a punk rock fan with a fake leather jacket and blue dyed bangs, has become a brunette again and favors hemp necklaces and clove cigarettes. She has confided in me about the marijuana plants that grow on the roof of Arthur’s parents’ townhouse and claims she doesn’t smoke pot because it makes her contacts dry out. Her father, who is now my ex-husband, is not so sure. We had a good divorce—if you can have a good divorce. Naomi spends most of her time anyway in Arthur’s huge Greenwich Village townhouse, so it was as if she had divorced us too. One night, Naomi arrives home with flushed cheeks and announces she is no longer a virgin.

“But I thought you would have done it already,” I stupidly say. Naomi’s mouth pops wide open.

“Do you think I’m a slut, Mom?” she shouts.

“But surely don’t all you girls…”

She slams the door before I can discuss birth control.

Harry is Naomi’s college boyfriend for all four years. They meet during freshman orientation and stayed together even the last semester of senior year. They are a wonder to their friends and their parents. Harry irritates my ex-husband by his constant grins and guffaws. He is the ultimate frat boy who cannot walk down the street without at least eight people giving him a high five. I do not understand how Naomi, after Arthur, can stand him. But Naomi has turned into a sorority girl with cute pink terrycloth skirts and white tennis sneakers and blonde streaks in her hair.

Even in winter, Harry wears flip-flops, t-shirts, and shorts. He is from Aspen and has the sharp, chiseled features of his mother, a famous Swedish model, with her blue eyes and high cheekbones. Harry is almost too pretty at times and he seems to compensate for this by always looking a grungy as possible.

“Hasn’t he heard of deodorant?” my annoyed ex mumbles to me during Parents Visiting Day. When Harry is accepted into business school in California, my ex and I share a bottle of champagne. Surely this is the end of a too long romance.

But we don’t have a real reason to worry. I receive a phone call from Naomi the night before her college graduation.

“Harry’s come out,” Naomi announces.

“Excuse me,” I ask, not sure about what I heard.

“Harry’s gay, Mom. I’m glad for him. I guess I kind of knew.”

I don’t ask any more questions. At graduation, Naomi poses with Harry and they embrace in front of the camera as if they are still a loving couple.

Two years later, I will see Harry in a film and then another film and another. But he has never admitted he is gay, although Naomi knows all about his string of lovers. Every time I see him in People magazine with a “new” fiancée I have to laugh. I never thought Harry was bright, but I never took him for a coward.

Owen is married. He is married with two beautiful kids and a beautiful wife. Naomi met Owen at the art gallery where she now works and he asked her to the Metropolitan Museum for advice since he knew nothing about art. There, in front of a Rembrandt, Naomi fell madly in love with him. Owen is twenty-five years older than Naomi and married to Jessica Carmel, a well-known opera singer who travels all over the world. So, there isn’t much to hide from Owen’s wife since she is so rarely in New York. But still. Owen is married, and I am the mother wolf.

I follow Owen from work one day (he also works in publishing and I know where his office is) and confront him directly outside Radio Music City Hall.

“I am Naomi’s mother,” I tell him. “Please leave her alone.” Owen stares at me for a moment, switches off his mobile phone and sighs. He is a very handsome man with neat gray hair and very blue eyes.

“I know it’s not fair,” he answers. “It’s wrong but I don’t know what to do. She’s threatened to kill herself if I leave her.”

I immediately take the train to Brooklyn and ring Naomi’s buzzer. When she opens the door, she is eating a yogurt and wearing sweats. She does not look like a suicidal young woman.

“Is it true?” I ask her. “Would you really kill yourself if Owen left you?”

She nods solemnly. I fight the urge to call the police, her father, my husband. The stricken look on her face is the same I saw in 11th grade when she waited hours to see Josh and his band and he walked by her without giving her a glance.

But I needn’t have worried. Six months later Naomi met Rajiv.

Naomi has quit her job and, with an inheritance from my aunt, has bought discount around-the-world tickets. She begins in Australia and makes her way through distant continents. In Mumbai, she meets a young man from India named Rajiv, an engineer who lives in Jersey City. When she introduces us to Rajiv, they are so in love that they gaze into each other’s eyes even when talking to other people. He is tall and funny and loves to cook and sing country western songs. Naomi moves in with Rajiv to his small Jersey City apartment and finds a job teaching art history at a charter school. Naomi’s father, my second husband, and I are relieved. She has finally found her true love. One afternoon, Naomi arrives at my apartment with a bouquet of roses.

“Thank you,” I tell her.

“They aren’t for you, Mom. They’re for Rose. That’s why I brought roses.”

“Who is Rose?” I ask. Then I see the blush rise in her face and I understand. She is three months pregnant and instinctively knows that the baby will be a girl. I place the bouquet in my favorite crystal vase and we toast with ginger ale. Finally, happiness. She and Rajiv fly to London to visit his parents. She will be gone for a week and during that time I obsessively shop in every baby store in Manhattan and buy the most beautiful baby dresses ever made.

She is due home the Friday before July 4th. We all plan to watch the fireworks from their Jersey City apartment rooftop. When Rajiv telephones me, I think we have a bad connection because his voice sounds like he’s underwater. I hand the phone over to my husband who listens, nods, and then starts to sob.

“My God, what happened?” I scream, I know. I know. My Naomi is gone. A brain aneurysm on the return flight from London. No one could do anything. These things happen. A famous actor’s daughter had suffered the same fate a month ago and the story was in all the papers. I have lost not only my daughter but my granddaughter as well. Rajiv arrives at our apartment, but I cannot see him. I hear his and my husband’s voices outside my bedroom door. I do not leave my bed for three days. Darkness is what I crave. Utter darkness. I lie on my bed, still and silent, like Naomi, like my daughter. Dead yet not dead, which is worse.

Somehow with the aid of drugs and my husband’s and ex-husband’s support, I make it to the funeral. The rabbi speaks to me, but I can’t see him in my blur of tears. In one corner of the room, I see a group of men. Some converse with each other while others are quiet. There are no women or children with them. All of the men wear beautiful suits. And then I understand. These men are Naomi’s past boyfriends. They approach me and one by one embrace me briefly and say a few words. Jack has grown up to look exactly like his father and is an emergency doctor in Maine with twin girls. He’s six foot two with a bushy beard and it’s so hard to imagine him twirling about in Naomi’s shimmery Tinker Bell costume. Pedro, who lives in L.A. and was contacted by a mutual friend about Naomi, is tall and handsome and has long lost his Spanish accent. Arthur, Naomi’s long-haired hippie, is now bald and a corporate lawyer in Washington. Harry wears sunglasses to hide his celebrity as well as tears. Owen is here, too. He seems to have aged at least twenty years and blows his nose in a monogrammed handkerchief. He tells me he is heartbroken for any pain he caused my daughter. Another man, a good-looking man with dark glistening hair and deep-set eyes, approaches me and takes my hand.

“I am so sorry for your loss,” he says softly.

“Who are you?” I ask.

“Josh. I knew Naomi in high school.”

I stare and stare. The long-lost love of her life.

“You’re too late,” I say.

“We are all too late,” he tells me, rubbing his eyes.

Finally, when the funeral is over, I take the pills the doctor prescribed and tell my husband I need to be alone in our room. But sleep or any sort of relief does not come easily. The only memories that bring me any sort of relief are the faces of Naomi’s boyfriends—all of them traveling hundreds of miles to be at her side today. They’re not boys anymore—they are men.

I drink a glass of water and walk unsteadily to my computer and begin to write about Naomi. Somehow my girl, my lost girl, has escaped me. Then I wonder if I really did see all the boyfriends or was I just hallucinating? No matter. I am comforted by the vision, real or otherwise, that I witnessed today. I can’t bring Naomi back but I am compelled to write the names of her boyfriends.

As I write this list, Naomi appears before me, laughing and shaking her head as she tells me of her latest romantic obsession.


Penny Jackson is the author of the novel Becoming The Butlers and the short story collection L.A. Child. She is also a playwright and screenwriter. Visit her at