Waiting for Emily

Friendship Romance Sad

This story contains themes or mentions of mental health issues.

Written in response to: "Your character is waiting — or yearning — for something or someone." as part of In the Dark.

Winston Shelby sat at the city bus stop waiting for Emily to arrive even though Emily had died over twenty years ago. He held a collection of cut flowers as he sat there wearing a suit jacket and a bow tie. No one seemed to notice him as he sat there in front of the abandoned Brownville Psychiatric Hospital. History had not been kind to the hospital as it closed its doors in 1965 after several complaints lodged against them with the deaths of several patients including Emily Dubeck.

The city council worked hard to find a contractor willing to tear the old hospital down and put in a new mall or something to make the community forget what had happened here in 1965. But every time someone did express an interest, something would happen and Brownsville Psychiatric Hospital remained right where it had been since 1935.

Upon closing, all the medical equipment remained right where it had been left when the doors closed for the last time. The foreboding red brick edifice had several broken windows from a number of vagrants who populated the neighborhood.

An elderly woman was strolling by when she saw Winston sitting on the bench with the flowers in his hand.

“Whacha doin’ here, young man?” She asked with her head tilted. She knew no one came this way unless they were looking for trouble, but he was dressed up.

“I am waiting for Emily.” He answered politely as the flowers moved in his hand.

“Is that so?” She put her hands on her hips, “Is she meeting ya here?”

“Yes.” He nodded smiling.

“Whacha name”

“Winston Sheby.” He nodded.

“Good to meetcha, I’m Selma Tucker.” She held out her hand. Winston looked at the skinny skeletal claw. Selma seemed nice enough, but he had bee told not to talk to strangers and her hand gave Winston a feeling of uneasy trepidation. When he did not shake her hand, Selma withdrew it and put her hand in her coat pocket. As nice as he appeared to be, Selma felt there was something odd about him as he sat there.

“Emily is my girlfriend.” He said without any provocation, but his voice had a flat affect as he spoke. His head swiveled as if it had come loose sitting on his neck.

“And this is the girl you’re waiting for?” Selma sat next to Winston on the bench.

“Yessum.” Winston nodded.

“Is she a special young lady?” Selma smiled.

“She sure is.” Winston continued to nod.

“People need someone special to make their lives happy.” Selma opened her pocketbook to check to make sure she had the bus fare.

“Where are you going? Winston asked.

“I’m going to visit my daughter.” She eyed him, because she was still a little leery of his intentions. She had lived in this neighborhood most of her life and knew how things could become if you weren’t paying attention. “She’s gonna have her third child.”

“That’s great.” Winston smiled.

“Are you and Emily planning on having children?” She asked, btu Winston looked at her strangely and shook his head. “You should. Having children is wonderful experience.”

“It is?” Winston was still shaking his head.

“Ah, here comes the bus.” She pointed to the city bus that was snaking its way down the road. She stood up as the bus pulled to the curve and the door swished open. “You take care, Winston.”

“You too.” He nodded as the doors closed and Selma was whisked away. She seemed like a nice lady, but Winston was glad she was gone. He did not feel comfortable talking to her any longer. When he talked about Emily, most people looked at him funny. He did not like it.

Winston Shelby was brought to the Brownsville Psychiatric Hospital in September 1959 when the school psychologist declared the twelve-year-old clinically incurably insane. Living with Mildred, his single mother who had been told most of Wiston’s life that something was definitely wrong with him, she was given few options either take him to a special school which she could not afford or dump him at Brownsville where one day they could find a cure. Mildred believed them when they told her this and so she had him committed.

Back then there was only one way out of the hospital, you either got better or you stayed committed there. Some of the patients he met had been there for years making absolutely no progress. A few of the older male patients liked young boys and would often try to lure them into their rooms with the promise of sweet treats. Winston had fallen for their ploys, but he quickly learned.

“What your name?” A girl his own age asked him once during lunch in the chow hall.

“Winston.” He answered as he leaned his head in his hand.

“That’s a funny name.” She giggled.

“Oh yeah, what’s your name?” He rolled his eyes to her as she slurped what was in her spoon.

“Emily.” She said with a belch.

“Girls are no supposed to burp.” He shook his head.

“In here they let me do what I want, because I am insane.” She informed him.

“Oh yeah, me too.” Winston shrugged.

“My daddy sent me here because I was misbehaving.” She shrugged back at him.

“They said I was insane at my school.” Winston shook his head.

“My daddy likes to drink.” Emily spoke as if this was common. “Men drink.”

“I wouldn’t know, my daddy went away.” Winston sighed.

“How come?” She picked her nose as she asked.

“Because of me.” Winston sounded hurt by his admission.

“Oh.” She tilted her head. “My mother died.”

“I’m sorry.” He genuinely apologized to her.

“What grade were you in?”

“I was in the eighth grade.” He managed to smile.

“I would be in the eighth grade, too.” She returned his smile. “Ya know they let us play in the gym after lunch. Do you wanna shoot hoops?”

“What’s that?”

“Basketball, silly.” She wore a smile that covered most of her face. Emily’s hair was brown with golden streaks in it, but her curls were never properly combed. With brown eyes that seem to be able to penetrate thick walls and a crooked smile, Winston was quite taken with her.

“Sure. I’ll play basketball.” He nodded. His Uncle Hank would take him to the playground to play. Uncle Hank, his mother’s older brother, had been a basketball star in high school until he hurt his knee and was never able to run again.

She taught him how to play HORSE and Winston loved the game.

“Hey cutie, wanna come by my room later.” An older man asked as he took a shot at the netless basket.

“What for?” She asked squinting at the gray-haired man with hair the same color on his chest poking through his tank top.

“I got some smokes.” He chuckled as he made another shot that went through the hoop.

“Sure.” She winked as he got the ball and dribbled toward the hoop.

“Do you smoke?” Winston was horrified.

“Don’t you?” She shook her head.

“No, I don’t.” He grimaced. “It’s yucky.”

“Oh, you will smoke and not think it’s yucky.”

He found out what Bruce wanted her to do for the cigarettes, and it made him ill.

The next day he sat with her at lunch.

“Why did you do that?” He asked her.

“Do what?” She frowned.

“You know…for the cigarettes.”

“Shut up.” She growled at him, “I do what I want and get what I want.”

“It’s not right.”

“Says who?”

“Says my mom.” Winston shook his head.

“Your mom doesn’t know how things work in the place.” She sneered at him.

“It doesn’t have to work like that.” He shot back.

“You know, I think you’re a snitch.” She pointed an accusatory finger at him, “And snitches here get what’s coming to them.”

Emily rose to her feet and walked away from him. Winston could not help but watch her leave the chow hall.

It took two weeks before he saw Emily again. They sat in the gym in the bleachers.

“Bruse and me are no more.” She told him.

“Oh?” Winston could not help but smile.

“He’s got someone else.” She shook her head.

“Good.” Winston was still smiling.

“You wanna go steady?” She asked as she blinked.

“Sure.” He nodded, “What do I have to do?”

“Be good to me.” She put her hands on his lapels.

“I can do that.” He agreed.

“C’mon let’s go outside in the yard.” She slapped him on the shoulder. He followed her out the door into the hall. As they passed a closed door, Emily pointed, “See that room?”

“Yeah.” He shrugged.

“They put people in there who are bad. It’s called isolation. They put me in there, but I wasn’t bad.” She began to tremble. “The walls are padded, because some people will hurt themselves in that room.”

Winston stopped and stared at the closed door.

“I don’t ever want to go in there.” He told her.

“You gotta do what they tell ya to do.” She bit her lip as the trauma continued to shudder through her body. “Or else.” She pointed to the door.

Reading the sign on the door, “Isolation Room,” Winston shuddered just thinking about what was inside. Swallowing hard, Winston followed her out into the yard.

Winston went steady with Emily for the next four years. Days passed like the fluffy clouds in the sky. Emily was developing more socially appropriate behaviors according to Dr. Lockett, her psychiatrist. Winston was too afraid to step out of line after seeing the Isolation Room. Emily told him that Bruce had spent a week there after beating up his girlfriend. Once again, the council wondered if it was not wise to separate male and female patients. The sexual tension could be hard to control, but a lot of the patients preferred same-sex relationships anyway.

Mildred visited Winston once a month. When he saw her in the family room, he noticed the dark bags under her eyes and a few more teeth absent. He would hold her hand as she talked about some of the men she had been with and the abuse, she had put up with.

“Tell them to take a hike.” He would shake his head.

“I need them. I can’t afford groceries or rent unless I have them.” She would throw her head back in dismay.

“I wish there was something I could do.” He would look away ashamed that he was helpless. When Winston talked to Dr. Henderson about being released from Brownsville, Henderson would review the records. Since he had followed the rules, Winston was showing progress, but with his diagnosis, Dr. Henderson reasoned that discharging was too risky. One of the hospitals had discharged a patient who then murdered his parents just hours afterwards. Reasoning that Winston was capable of doing this, he always ruled against his discharge.

“I talked to your doctor, son, and he says discharging you could be a mistake.” She dropped her gaze to her wrinkled hands folded on the table between them. “I’m just not sure. I wish I could be. You seem like you’re ready to come home. I kept your room picked up for you, too.”

Tears began to fall on her sunken cheeks.

“Heaven knows I could sure use your help at home.” She wiped her tears with the back of her hand.

“I could get a job, and you wouldn’t need anybody else.” He inhaled.

“I will ask again. I promise.” She squeezed his hand. She would never have a chance, because her current boyfriend beat her to death a week later. Winston wasn’t given time to go to her funeral. When he got angry during process group with Dr. Henderson, he was remanded to the Isolation Room for twenty-four hour cooling off.

Emily was sitting on the bench outside the room, waiting for him. They hugged and kissed.

“I asked if we could get married.” She looked into his eyes, “And they said we could, but we would have to live in our own rooms.”

“Alright.” Winston kissed her on the cheek.

“I love you, Winston.” She whispered.

“I love you too, Emily.” He whispered back.

“This is highly unusual.” Dr. Henderson said at their next meeting, “Winston, patients getting married is not well advised.”

“But I love her.” He countered.

“Love is special, but in this hospital, it can create difficulties.” He held out his hands.

“I was told I could marry Emily.” He folded his arms across his chest as a gesture of defiance.

“Well, the council thinks you have earned this privilege, but I voiced my reservations.” He shook his head.

“If you had discharged me when my mom came, she’d still be alive.” Winston shook his head.

Dr. Henderson knew that Winston still harbored some resentment over that issue, but he acted in the best interests of the patient. The death of Mildred Shelby was unfortunate, but it was not the fault of the hospital.

Despite his reservation, the board ruled in favor of Winston and Emily’s wedding. It would be looked at as good public relations since there was negative publicity in some hospitals about the dreadful treatment of patients in their care.

Bruce was waiting for Emily in the yard one day after the wedding was announced.

“So you gonna marry that pansy?” He leaned against the chair link fence.

“Yes.” She said taking a shot with the basketball she held.

“You’re makin’ a mistake.” Bruce laughed as he put his hand to her throat. Emily gasped for air. From out of nowhere, Winston hit Bruce in the midsection. Bruce doubled over with a groan. “Son of a-“

Another blow brought him to his knees. One of the orderlies grabbed Winston. No one saw the shard of glass in Emily’s hand. In one motion, Emily sliced Bruce’s throat with the glass.

Bruce would not survive the ambulance ride. Emily was put in handcuffs when law enforcement arrived. As she was led away, Dr. Henderson told her that the wedding was off.

A week later, Emily hanged herself in her cell because one of the guards did not check her cell close enough.

She left a note to Winston:

Dear Winston,

I love you very much and I cannot bear my life without you. Please understand that this is the only way. Please wait for me. One day we will be together again.

Love,

Emily

The service was short and bittersweet as Winston was allowed to attend under heavy surveillance. The following year, the hospital was closed down and Winston was discharged. He knew he had to follow the rules or wind up going to another hospital somewhere.

He would sit waiting until one of the patrol officers who had gotten to know him would send him back to his boarding house. It was hard for the officer to believe, he was still waiting for Emily after all this time.

Posted Jun 13, 2026
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