The Undateable Man

Submitted into Contest #194 in response to: Write a story inspired by the phrase “Back to square one.”... view prompt



Edward Allen thought himself to be a fairly simple man. In fact, he lived off of three things: meat, beer, and Gunsmoke. 

   Edward was in quite a predicament, though. A dreaded state of repetition. Recently, he reached the part of his life where loneliness was a boulder in his path. So, after exclusively researching the concept of “first dates,” Edward went out to buy a tailored, navy blue suit. He squandered up some money to be able to afford to eat at Fabio’s, the neighborhood sit-down restaurant. He got his too-long ginger hair cut above his ears. And he paid a visit to the florist across from Fabio’s. 

   Ultimately, Edward Allen found himself a date. 

   His first date’s name was Emily Apple. Edward had heard of Miss Apple through the grapevine and insisted to take her out to the finest restaurant in all of town. To his delight, she agreed.

   At exactly six o’clock, Edward was seated at a two-person table in the very front of Fabio’s. He placed the cherry-red carnations on the tablecloth. Then promptly shifted them because they didn’t look right. One more time for good measure. He reached into the inside pocket of his suit jacket, fishing out a pen and a yellow pad of paper. At the top, he wrote, Analysis of Emily Apple: To Date or Not to Date.

   Edward looked at his watch. Frowned. Then scribbled the first bullet point: Not on time. 

   Just as he finished, a pair of bright green eyes appeared in the seat before him. Edward marveled at the sight of her: a petite blondie with a pretty smile and round puppy eyes. Emily Apple wore a nice wine-colored dress, her shining hair cascading down her chest. Satisfied with her complexion, Edward smiled and pushed the notepad aside. 

   “You must be Edward!” The plump, pink lips not far from the green eyes fired into a quick smile. “This city traffic is so rich! My apology for bein’ so late. I’m Emily. It’s nice to meet ya!”

   Kindly, Edward nodded. “Good evening, Miss Apple. Not to worry. I also fall victim to the Pennsylvania traffic. 

   He picked up his pen while Emily took her seat. Green eyes, similar to snakes. 

   Said eyes flicked from Edward’s face to the pad he wrote on. Emily’s lips twitched downwards, only slightly. 

   “Those carnations are for you,” Edward said without looking up. 

   “Oh, wow! These are just stunnin’, Edward! How thoughtful.”

   Edward grinned, finally putting his pen to rest. “Tell me about yourself.”

   Emily Apple strung a piece of straw-blonde hair around her finger. “Well. I just moved from Kentucky-”

   Thick accent, hard to understand. 

   “-to live with my mama for a while, but I’m lookin’ to live here-”

   Lives with parents. 

   “-permanently.” Emily’s frown deepened. She looked slightly disgusted. “I’m sorry, what’s the notepad for?”

   “Just some notes,” Edward told her innocently. “For future reference.”

   “Uh-huh.” The small woman appeared disputed. Edward didn’t know why - wasn’t he supposed to gather information on a first date? After all, that’s what one of the websites he’d scoured told him to do. To collect as much as he could about the woman in question. But then again, he wasn’t the one with the problem. It was Emily Apple. 

   Just in time, a waitress came around to collect their orders. 

   Like a gentleman, Edward let Emily order first. His pen tapped restlessly against the table, eager to make any sort of judgment. Emily was not amused. She stared at him even though her menu was open in front of her, the waitress waiting for instruction. Edward blinked, disoriented. Emily sighed. 

   “I’ll take the garlic-butter steak, please.” Her voice was exasperated (and it was only the first few minutes of the night.) “And a glass of champagne.”

   Edward weighed her choices. If he was being honest, he would’ve ordered the same thing, if not for his pasta craving. So he set down the pen and faced the waitress, who looked ready to crawl under a nearby table at the tension between the two. 

   “I’ll do the chicken alfredo, but with shrimp instead of chicken, please. And a nice IPA, too.” 

   The waitress all but sprinted away, and Edward diverted his attention back to Emily Apple. Eying the notepad, she asked, “And what about you, Edward? What’s your life like?”

   Oh, he’d been waiting for this question! He leaned back casually, smiling at nothing in particular. “Well, Emily Apple, I think myself to be a fairly simple man. In fact, I live off of three things: meat, beer, and Gunsmoke.

   “That old T.V. show?” Her laugh was like popping sparks. “I didn’t even know that was on cable anymore. You must like Matt Dylan, then, hmm?”

   “More of a Festus kind of guy.”

   “Festus,” she mused. “Now isn’t that interestin’.”

   Edward watched in dismay as she propped her elbows on the table and dipped her chin into her hands, verdant eyes gazing right through him. 

   He penned his thoughts. 

   “Do you always summarize your dates?”

   The question caught Edward off-guard. “This is my first date.”

   Emily Apple’s eyes went wide with understanding. She looked to the ceiling and suddenly laughed. “Now that makes a lot of sense!”

   Edward frowned. 

   “Darlin’, don’t take my words to the heart. I’m just advisin’ you not to take notes on the first date. It makes you seem judgemental. Alright?”

   Edward lifted his chin in agreement. Then proceeded to scribble, Don’t take notes on the first date. It makes you seem judgemental. 

   And when he met Emily’s gaze again, she looked exasperated. 

   For the remainder of the night, the pair didn’t say much. They ate in utter silence. Edward wrote a few bullet points on her table manners - he couldn’t resist it. He enjoyed Emily Apple’s company and found to like her more when she wasn’t talking. Her face was a canvas of the thoughts that ran through her head. He could tell when she thought something he said was funny, or when it wasn’t. He could tell when her smiles were genuine, or when they weren’t. Miss Apple was an open book. 

   And, he could also tell that Emily hated it when he called her Emily Apple. 

   But it was the kind and respectable thing to do, so he kept doing it. He was proud of himself for sticking to his guns either way. 

   When Edward had paid for their dinner with displeasure - champagne was very expensive and Emily had gotten three glasses - Emily stood up very quickly, cradling her bouquet of flowers in her arms. She mumbled a thank-you and apologized for her hurry to be out, just that she didn’t want to be stuck in traffic again or something like that. 

   When she turned to leave, Edward grabbed her free hand. Her eyes read shock - Lord, those snaky eyes would be indented in his brain forever - but she didn’t pull away. 

   “Do call, Emily Apple,” Edward murmured. He smiled. 

   Emily beamed back and disappeared into the night. 

   He waited three weeks. Emily Apple did not call. 

   Edward thought he had done a good job. He went over his notes for the millionth time and found nothing wrong with it. So why did Miss Apple not call him, nor text him, nor make any mention of him to her friends? It made Edward slightly sad. 

   So he did the best he could do: go back to square one. 

   On a Friday night at six o’clock on the dot, Edward sat in that same table at Fabio’s, adjusting white carnations. The woman who would be meeting him tonight was named Erica Swanson. Erica Swanson was a friend of his sister’s, who, bless her heart, had arranged for Erica to meet up with him. Edward flipped to a fresh page in his notepad and sketched out, Analysis of Erica Swanson: To Date or Not to Date. He kept it to the side, just in case Erica was as sensitive as Emily Apple. He would have to scrutinize her in better privacy. 

   At 6:01 exactly, Edward watched a tan, ebony-eyed woman stride over to him with an important expression on her face. She looked like the word business. Slender black dress and satin-like brunette hair. Her movements were fluid, like water. And when she took her seat, her lips folded into the kind of smile you’d see at an interview. 

   “Hi, Edward.” Her voice was exactly what Edward had expected - calm, monotonous, business-like. “I’m Erica.”

 Edward wrote without looking, Probably invests in many stocks. 

“Good evening, Erica. How was the drive?”

“Oh, quite nice, thank you.” Her gaze drifted across the flowers for a split second. “Are these for me?”

Didn’t wait for me to offer the bouquet. “Yes, they are. I hope you like carnations.” 

“You’re in luck, I do! Very kind of you, Mr. Allen. Thanks.”

He smiled - he liked that she addressed him with his last name, as it should be. “How has your day been?” he asked - if only to fill the silence.

“Terribly busy,” she sighed. “I work for a corporation and all they do is send me on errands and waste my gas! In this economy? It’s irrational. But my boss-“

Okay, now Erica Swanson was losing him. He nodded along anyway, diverting his attention to writing, Very wordy. 

Miss Swanson rambled on about the broken coffee machine in her office and didn’t notice him taking notes. Edward waited patiently for Erica to finish her story, pretending to pay attention even though she wasn’t looking at him. The same waitress from last time rolled around, glancing between Edward and Erica with a befuddled expression. She dropped off waters and said she’d give them more time, still looking at Edward like he had an extra head. Odd. 

Thirty minutes later, Edward began to tire of Erica’s never-ending tale. She hadn’t even asked him a question about himself, nonetheless let him say a single word. By the time their food arrived - Edward had caved in and decided on the garlic-butter steak, while Erica had gotten chicken parm - he was desperate to get out of there. Subconsciously he wondered if this was how Emily Apple felt on their date. But then he realized that it was absurd, since he was a good man, and settled on women being the problem. 

The woman finally fell silent as they ate their meals - to Edward’s relief, she ate very daintily and slowly - so he took his chance at setting the bar. 

“Well, I’ll tell you this, Miss Swanson,” he said. “I think myself to be a fairly simple man. In fact, I live off of three things: meat, beer, and Gunsmoke.”

Erica’s fork stopped midair. 

Her face went completely blank, a perfect picture of shock. She set down her cutlery and looked Edward straight in the eyes when she said, “I truly apologize, but it’s getting late. I should be going.” 

Edward was quick to get to his feet, startled. “It’s hardly seven.”

“A smidge too late for me.”

“Oh.” Something about Erica’s tone hurt his pride. “Well… do call, Miss Swanson.”

Erica didn’t smile, not like Emily Apple did. She gathered her carnations and murmured, “Surely,” before hurrying out of the restaurant. 

Edward thought that the date went fairly well, and if not, at least Erica Swanson didn’t contradict his note-taking abilities. They barely even had a conversation. So he paid for the dinner and left with happy thoughts about his future.

One week ticked by. 

Then two. 

Erica Swanson did not call.

Edward was getting discouraged. According to an article he read before dating, he should have secured a second date by now. Was it his suit? Did the women think it was tacky? Or was his hair too short? Edward thought he was slick with his words, with explaining why he leads a simpler life. It should be a set deal after that! So why did his dates always insist on leaving right after he spoke? That just made him furious. He completely wasn’t the problem. 

So, with his fury in mind, he set up one last date. 

This was one with a woman named Jessica Walker. Edward had met her online, through a dating site he found while researching. She lived in the same vicinity as him, just across town. She was a hair stylist, owned a dog, and enjoyed taking hikes. So Edward decided that Jessica was his next victim and shot her a message. In his triumph, she responded almost simultaneously, expressing that she loved Fabio’s and would be there exactly at six o’clock the following Friday. 

That surprised Edward. His hopes rose exceedingly high. 

On that Friday, Edward walked into Fabio’s with a smile already on his face. He strolled up to the hostess, who gave him a familiar grin. 

“Back again,” she noted. “But this time, you aren’t first. Your date is already here.”

Edward’s eyes went wide. “Really?”

The copper-eyed hostess nodded. “She seems very nice. I hope everything goes well.”

Edward thanked the kind girl as she lead him to the customary white-clad table, suddenly eager. Finally! Someone who held punctualiaty dear to the heart as Edward did. Ecstatic, he practically leered into his seat, beholding the lady already sat at the table. 

And she was perfect. 

Stunning, dark auburn curls that sat softly against her shoulders. Merry violet eyes that crinkled as her face lit up with a cherry smile. Button nose, midnight blue gown, silver jewlery and dainty hands. Edward was dumbfounded by her.

He was already in love. 

“Good evening! You must be Edward Allen.” She stood on sweet, long legs to shake his hand. 

Edward almost couldn’t find words. “That’s me. Good evening to you, too, Jessica Walker.” He offered up blush-pink carnations. “I picked these up for you.”

Jessica’s smile went larger. “Oh, dear, these are wonderful! Carnations are the prettiest.”

The pair sat at their table, and, Edward had to admit, they hit it off instantly. Jessica Walker was like a firework. She had her own apartment, was from Pennsylvania, wanted to be a photographer, didn’t speak about herself too often, had a crisp American accent, and she was funny. So funny! They exchanged jokes every few minutes, laughing until their eyes watered. The other people in the restaurant gave them looks, but Edward didn’t care. He was having too great of a time. 

And when the same waitress - who didn’t appear surprised that Edward was back, and actually greeted him by name - came over to collect their order, Edward and Jessica found themselves ordering the exact same thing. Chicken parm! Jessica exclaimed how much she loved the chicken parm, and, though Edward had never gotten the chicken parm and was only getting it because it looked scrumptious when Erica Swanson ate it, he agreed with her. 

He didn’t even pull out his notepad the entire night. His mind was made, and he was sure nothing could deter him. 

At the very end of their date, they stood at the front door of Fabio’s, about to bid there goodbyes. Edward felt so relaxed and casual. No one had ever made him feel so comfortable before. Jessica Walker and Edward shared the same brain, the same wavelength. It was bound to be a perfect love story. 

“Well, Edward Allen, I’ll tell you this,” Jessica Walker said. The moonlight lit up her heart-shaped face, making Edward captivated. “I like to think that I’m a very basic woman. In fact, I live off of three things: wine, bread, and Golden Girls.” 

Edward frowned. Hard. 

That was absurd! Nobody could be that basic. It was immodest, petty, cocky! All of the good things about Jessica Walker immediately turned fake. All of her smiles, jokes, and words were suddenly shiny plastic. So she was just playing him? She was putting on a show to make it seem like she was experienced in the art of love? Edward was disappointed - no, he was devastated. All of those websites were a waste. 

While Edward mentally wallowed, Jessica teetered on her heels awkwardly. “I had a great time, Edward. Call me!”

In a flurry of dark fabric, she was gone, leaving Edward inwardly exhausted and vowing never to date again.

Needless to say, Edward Allen did not call Jessica Walker. And it was back to square one for them both. 

April 21, 2023 23:28

You must sign up or log in to submit a comment.


Mary Bendickson
12:43 Apr 22, 2023

Charming and sad and funny. And such is the dating life. I wish Edward Allen well but...Back to square one!


Akhlys Ivy
16:13 Apr 22, 2023

Hahaha! I’m glad you liked it!!! :)


Show 0 replies
Show 1 reply
RBE | Illustrated Short Stories | 2024-06

Bring your short stories to life

Fuse character, story, and conflict with tools in Reedsy Studio. 100% free.