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The Date - a Short Story

Updated on May 20, 2022

After years of dating, Jill is at the end of her rope. Will this be just one more dating disaster?

Jill hoped her date was ugly.

Then she'd be able to get out of there fast and take care of some very important sock-sorting she’d been meaning to catch up on. But no, of course he wasn't ugly at all, he was actually pretty cute - so his fatal flaw was obviously going to be something else.

Jill hadn't always been this bitter - she could remember when she was just another happy, naive 20-something girl. As she smiled at her approaching suitor, Jill was suddenly back on another date. The man in front of her was named Ronny.

Online, Ronny’d seemed incredible - a degree from Duke, a job as a high level statistician - and Jill had been impressed. When she’d met him at a local bar, he’d talked about himself for 92.4 percent of the evening. When Jill had had the temerity to talk about herself, he’d put her in her place by giving her an unsolicited primer in actuary charts. As far as Jill was concerned, Ronny was in actuality a moron.

Then there’d been Jeff. Jeff had been introduced to Jill at a party and after 5 vodka gimlets he’d seemed fascinating - the tortured creative type. As it turned out, it was torture to be with him.

Larry was hilarious, and Jill had thought he’d really be a great time. He was - for everyone in the restaurant. After 3 hours of watching him crack jokes with the waiters, yell across the bar bantering with the other patrons, and dance BY HIMSELF to “It’s Raining Men”, Jill’s head was so far into her turtleneck that she thought she would suffocate.

“Is everything all right?” he asked.

“Well I...oh!” Jill jerked her head up, startled. It was this new person. Alright, better get this disaster over with.

“Sorry about that.” She was instantly annoyed - he had a great smile. “I guess I drifted off there for a minute.”

He looked like he knew what she’d been thinking. “No problem,” he said warmly. “I was just asking about your trip to New Zealand. Sounds fascinating!”

Damn that profile.

Jill remembered her girlfriends convincing her to sign up for online dating. “Come on, Jill,” they’d whined at her. “You’re not meeting anyone, and this is supposed to be the best site! It’ll be fun!” Of course they would say that - they were all married.

She’d had to fill out form after online form, disclosing her interests (finding a man who was quasi-human), her history (dating men who were not quasi-human), and her aspirations (see the first one). She’d submitted to all that the words on the screen had directed her to do, and then clicked “submit”. And waited.

At gottagetadate, apparently, a good prospect was Vince. Vince was absolutely gorgeous. Too gorgeous for women, as it turned out, but gorgeous. The night wasn’t a total loss, though - Jill learned how to apply lip liner.

“So we started in Auckland...” As she told - what was his name again? about her recent trip to New Zealand, where she hadn’t had to date and had had the best time ever, Jill wondered how the algorithms at had computed that she would like Billy. Billy was sweet, funny, and warm - and so was his mom. Mom did his laundry, cut his meat, and Jill even whipped her head around one evening to find her giving him a back rub. “To ease his tension”, Mom had cooed. She’d avoided a confrontation by leaving one night while he and his mom were watching “The Way We Were” together.

“...and then Wellington...” And then, of course, there had been Scott. Scott had finally seemed like a viable contender, an oasis of normalcy in a desert of freaks. He was fun, nice, a brilliant tax attorney - and Jill and he had gotten to the “L” word. She'd felt like this was it. Scott had even proposed, and Jill had said yes. That’s when the trouble had begun. It seemed as though as soon as they’d started calling caterers, Scott was suddenly never around. Jill would ask him what was wrong, and he’d say “Nothing, honey” with a distant look in his eyes. The following month all that was left of Scott was a note explaining how he wasn’t ready for marriage and blah, blah, blah...Jill had blocked out the rest of it.

“The thing is, I’m perfectly fine being alone - I don’t want just anybody as a mate.” The guy - Barry, that was his name - was talking. She looked at him cynically. Was he just saying that because he knew that was her attitude? Wait, he couldn’t know that; she hadn’t put that on her computer profile.

“...You too?” She laughed nervously. She found herself suddenly not hating him, and that bothered her. As they smiled at each other again, Jill’s brain scrambled to find what was wrong with him.

She remembered back to Steve. Steve had been brilliant, insightful, and funny - and asked to borrow money to pay for the date. She thought quickly - she had enough for her half only. No way was she going to...

“Look, I’m sorry if this is coming out rude, but if you don’t want to be here you don’t have to be”, the Barry person said at her.

Jill stared at him, stunned.

“What? What are you talking about?” She felt her face get hot as a stab of embarrassment ran through her body.

“Look, I’m sorry. It’s just that this is not exactly easy for me, but I’m trying here.”

Jill looked at him.

“Neither of us is in our 20s any more - we’ve been through all this junk a million times, right?”

She nodded, her eyes wide.

“Well...I just think that I’m at the stage in my life where I don’t really want to do the BS dance any longer. So here, I’ll tell you: I have anxiety disorder. I’m on three different medications. I’ll probably always be on medications. And you know what? I’ll probably always be just a little bit crazy. I’m sloppy, I’m friends with my ex-girlfriend but not interested in her, and I am not organized. Other than that, I’m a working journalist, I’m honest, loyal, pretty smart, and love Monty Python. So there you have it. You can go back to judging me and thinking you’re superior to me, and who knows, maybe you are. All I know is that I’m done.”

Jill took his hand and finally spoke. “Thank you.”

As they looked into each other’s eyes, Jill’s phone rang. It was her just-in-case-I-need-to-escape call. Neither of them even heard it.


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