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  • Writer's pictureShelly Desjarlais

The Failed Romantic

Updated: Feb 2, 2021

February meant only one thing to Reagan: The return of Valentine’s Day. This was not a good thing, in her humble opinion. She leaned against the cash register with a scowl. It looked like Cupid had personally decorated the entire pharmacy. Chocolates, plastic roses, giant teddy bears, sappy cards—she was surrounded. Just great.

She loathed Valentine’s Day. Truly, wholly, deeply loathed it.

“Hey, Reagan, stop scowling. You’re going to scare the customers away!” the manager called.

She sighed heavily. “Sorry, Phil.”

“What’s with the long face anyhow? Don’t you have a date lined up for the fourteenth?”

“No, I don’t," she grumbled.

“Why not?" he asked. "I thought you had a girl.”

“I talk about a girl. That’s not the same as being with a girl.”

Phil wandered up to the counter, snapping his fingers. “C’mon, c’mon. Give me the scoop.”

“There’s not much to give,” Reagan returned. “I have this old friend who just got back to town, and I decided it’d be a swell idea to fall in love with her.”

“Uh-oh. Does she know how you feel?”

“Of course not. Even if she did, I’m a failed romantic.”

He snorted. “How can you be a failed romantic?”

“For the last five years, every Valentine’s Day has been a disaster.”

“What do you mean?”

Five years ago

Reagan’s car pulled up to the home of Lovely Lana. She was a beautiful gym teacher who lived in a two-story house. Reagan had her eye on Lana for the last few months. Now that it was Valentine’s Day, she was ready to swoop in like a true romantic.

The stereo was heavy in Reagan’s hands. It’d been hard to get a hold of a stereo in a digital age, but it had to be a stereo. She wanted to get that full cinema impact.

With gusto, Reagan set up under Lana’s window. She pressed the play button and held the stereo above her head. It sang out one of Reagan’s favorite love songs.

After a moment, the window opened. Lana stuck out her head. “Reagan?”

“Yeah. Happy Valentine’s Day, Lana.”

Lana grimaced. “I hate that song.”

“Oh. You do?”

“I seriously hate that song.”

Lana shut her window. Reagan sighed. So much for that idea.

Four years ago

Reagan drove up to the house of Beautiful Bethany. She was a brilliant historian at one of the local museums. Her duplex was cute and compact. Reagan hadn’t known Bethany long, but she was beyond smitten. Since it was Valentine’s Day yet again, Reagan was ready to give romance another go.

The bouquet of flowers was colorful. Reagan gripped the slick plastic wrap in her anxious hand. It was tough to find the perfect assortment. She felt roses were too simple, too expected. No, she went all out.

Reagan knocked on the door twice. Bethany answered with a smile. “Hello. This is a surprise.”

“Happy Valentine’s Day,” Reagan presented.

The moment Bethany took the flowers, she sneezed. She sneezed again and again, pushing them quickly back at Reagan. “I’m allergic!”

Promptly, Bethany slammed the door. Reagan could hear her sneezing through the wood. She sighed. “Well, that went about as well as last year…”

Three years ago

Reagan stopped outside of the apartment complex where Gorgeous Gina lived. Gina was the founder of a nonprofit organization devoted to saving the environment. Reagan had visited one of her fundraising booths at a street festival, and Reagan was taken by Gina’s sincere smile. With Valentine’s Day here, Reagan knew she had to do something special for Gina.

The gigantic Valentine’s Day card was hard to get up the steps. Reagan had written a sweet, albeit terrible, love poem inside. She awkwardly waddled to the right unit, holding the card behind her. There was no point to this, as it was still clear she had the huge thing in her hands. Still, she wanted a bit of theatre in her presentation.

After a few knocks, Gina came to the door. She had a look of amazement. “Reagan. Hello.”

“Hi. Happy Valentine’s Day!” Reagan fumbled with the card, but eventually she managed to hold it in front of her.

Gina crossed her arms. “Do you realize how many trees had to die in the making of that card?”

“Well, I—”

The door slammed. Reagan huffed. There went another Valentine’s Day.

Two years ago

Reagan parked in the lot outside of Sexy Sherri’s quaint shop. Reagan had met the attractive woman when she dropped by the shop for a birthday gift some months earlier. Sherri would be working late, Reagan knew. So, she thought she’d bring a bit of Valentine’s Day to her. It seemed like a good idea, but she knew her track record wasn’t so great with this sort of thing.

This time, Reagan had a box of chocolates. Everyone loved chocolate, right? Surely nothing could go wrong with that.

She walked into the shop with the box hidden under her coat. Sherri glanced up from the register, grinning. “Hi, Reagan.”

“Hey. It must be a bummer working on Valentine’s Day. I thought maybe I could bring the romance to you.”

Reagan mentally prided herself on the smooth opening. She revealed the box of chocolates with flare. Yes, this was going perfectly! Sherri even took the box.

“This is nice of you, but I’m a gluten-free diabetic vegan.”

Sherri handed the box back. Reagan stared blankly. “I see…”

“I’m also working,” Sherri hinted.

Reagan nodded her head. “I’ll be going then.”

What another marvelous February fourteenth.

One year ago

Reagan drove out to Attractive Amberly’s cabin just beyond town. She’d met Amberly on a hike not long ago. Amberly was a looker and had a brilliant mind. She had invited Reagan up to the cabin anytime. Valentine’s Day felt like the perfect anytime.

When she got to the cabin, Reagan lifted the adorable plush from the passenger’s seat. She didn’t want to go with a teddy bear. No, no. Too obvious. Instead, she had found a cute monkey with pink stripes and a plush heart. She congratulated herself on her original thinking. Amberly would surely appreciate that.

She knocked on the door a few times. Amberly opened it with enthusiasm. “Oh, hey! Reagan, nice to see you.”

“Nice to see you too. You’d told me that I could come up whenever, so I thought I’d drop by to wish you a happy Valentine’s Day.”

Reagan held out the monkey. Amberly began to scream in terror. She recoiled, flailing her arms wildly. “Get it away! Get it away! I’m terrified of monkeys!”

“You are?”

“There was an incident at the zoo when I was little. GET IT AWAY FROM ME!”

Amberly slammed the door. Reagan frowned and looked at the monkey. “Looks like it’s just me and you, buddy.”

This year

Phil whistled after hearing those tales. “Man, you really do strike out a lot.”

“Tell me something I don’t know,” she grunted.

He gave her an enthusiastic pat on the back. “Hey, by now you’re used to failure. So, why not give it another try with the girl you like this year? If it goes bad, you’re prepared. If it doesn’t suck, it’ll be a pleasant surprise. You feel me?”

“No, Phil. She’s different than the other girls. I’ve known her my whole life. I’ve loved her my whole life. I was scared to say it, and she moved away before I had the chance to get brave. Now that she’s back, well. I’d never forgive myself if I screwed up.”

“Before now, you’ve always gone after girls with some gimmick. Flowers, candy, monkeys—that kind of thing. Why don’t you go after this girl without all that stuff? Go to her door as yourself. You’re not half bad, you know. I bet you could do fine on your own. If you don’t try, you’ll never know what could’ve happened.”

She considered this. “You really think I should, huh?”

“Who’s the manager at this store?” he asked.

“Phil,” she answered.

“And who’s the employee who has to do what Phil says?” he continued.


“Phil says you have to try,” he spoke in third person. “I mean it. Try.”

Reagan reluctantly nodded her head. “Okay. I’ll give it a go.”

“That’s the spirit. If it goes bad, don’t hit the bottle too hard. I can’t have my best employee working with a hangover.”

Phil left Reagan at her register to ponder what she should say or do. How could she eloquently share her feelings? That was a hard thing to accomplish. She started to jot down a script on discarded receipts. Maybe if she had a speech in mind beforehand, she wouldn’t be so nervous. It was all about preparation, she figured. Simple, right?

On Valentine’s Day, she drove to her friend’s townhouse right after the sun had set. Reagan checked to be sure every hair was in place, and she mumbled her speech three or four times. After that, she left the safety of her car. It felt like her feet were filled with lead as she walked to the front porch. She was about to turn back when the door opened.

“I thought I heard that clunker of yours,” her friend commented.

Everything Reagan had written and rehearsed was forgotten. She was going to have to wing it.

“Hi, Judith. I was just. You know, I work right down the road and. Well, I wanted to. Um…”


Reagan sucked in a deep breath. “I’m here because it’s Valentine’s Day. The problem is that I’m not romantic. I’m not really that smooth either. I’m awkward and clumsy, especially when it counts. I’ve tried to be suave before. You know, like that person who can sweep a gal off her feet and then carry her off into a sunset. But that’s not me. I’m an average girl who’s fallen in love with an extraordinary one. I haven’t had the guts to tell her. Since today is supposedly a romantic occasion, I thought I’d try. Would you get a drink with me? No strings attached. Just a chance for me to show you how I actually feel.”

Judith absorbed this speech. She answered slowly. “You are awkward.”

“Painfully awkward,” Reagan somberly agreed. She assumed this was another rejection. “I’m sorry for bothering you. I shouldn’t have said anything.”

Reagan turned and headed towards her car. Judith jogged to catch up. “Wait. Reagan, I didn’t mean that in a bad way. I like your awkwardness.”


“Yeah. For someone who’s not romantic, that was one hell of a romantic speech. Definitely the most romantic thing anyone’s said to me.”

“You’re serious?”

“Serious. I was waiting to see how long it’d take you to tell me how you feel. It’s kind of obvious.”

“Why didn’t you ask me about it?”

“And have missed a moment like this? Not a chance.”

Reagan smiled with a tinge of embarrassment. “Does that mean you’ll get a drink with me?”

“Let me grab a coat.”

Judith returned to her house to grab her coat. She climbed into Reagan’s car to head out for the nearest bar. Reagan couldn’t believe that finally she had experienced a beautiful Valentine’s Day. Several years down the road, she’d give another speech for Judith on February fourteenth. This one would be a proposal.

She’d say yes.

--Happy Valentine’s Day!

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