Below you’ll find my (unedited) entry for Round 1 of the NYC Midnight Rhyming Story Challenge 2025.
My prompt was:
Genre: Romance
Theme: The benefit of the doubt
Emotion: Exhilarated
Synopsis:
A guy about to graduate college is questioning his decision to admire his crush from afar, instead of making a move.
I’ve had this crush for so damn long,
my friends grew bored of poking fun.
“Just ask him out, man, while we’re young,”
They sigh, while I just freeze or run.
I’d rather watch him from afar;
he’d never want me anyway.
He plays guitar at Tommy’s bar,
though entry’s free, I’d gladly pay.
I’m boring, average, and shy,
but Dylan’s funny, smart, and…nice.
And while I dream, the years fly by.
My friends all date; I fantasise.
As graduation’s drawing near,
I’m feeling stressed and losing sleep.
I don’t know what has caused this fear;
it’s too intense and runs too deep.
When walking from our final class,
he brushes past, the penny drops.
To face my fear I cannot pass
this chance to ask him, so I stop.
It’s now or never… “Dylan? Hi.”
He turns his head expectantly.
“Would you…” I swallow, throat gone dry,
“Would you go on a date with me?”
He stares at me for quite some time.
His eyes search mine, I watch him frown.
The silence stretches…I resign
to feel my world come crashing down.
I try to speak, to take it back,
but then he answers, “Yeah, alright.”
To process that, I need a sec.
I suddenly feel very light.
We settle on a coffee date,
I must be grinning like a fool.
He smiles, but seems to hesitate;
I have to try to play it cool.
The day before our date I spend
obsessing, fretting, freaking out.
I know that I should tell my friends,
but what if Dylan’s doubts win out?
I’m early, but, to my surprise
I’m not the first one to arrive.
We order drinks, I meet his eyes.
A spark takes hold, I feel alive.
Our conversation stops and starts,
I talk too much, or not enough.
He’s guarded, while I try too hard.
Reality is pretty rough.
Well, this is it, at least I know
that we were never meant to be.
He signals that it’s time to go
and who am I to disagree?
We walk in silence, when he says:
“The park is nice this time of year…”
All I can manage is a “Yes?”
He looks at me, his smile sincere.
He talks about this job he found;
it’s out of town, he’ll have to leave.
We take a seat on sun-warmed ground.
He sighs, lies down, tugs on my sleeve.
We stare and watch the clouds float past.
He moves his hand, it’s touching mine.
I want to make this moment last
and let our fingers intertwine.
The sun, the grass, the breeze, his skin…
I try to memorise it all.
This moment’s real; I crack a grin.
A victory, however small.
I’m sure my friends will give me hell
for waiting till the very end.
But even if this is farewell,
it beats the times I played pretend.
I placed 4th in my group, which means I made it to Round 2 this year.
Click here to read the feedback I received from the judges.
WHAT THE JUDGES LIKED ABOUT YOUR STORY –
- {2144} I really like this story. I think you do a good job of accurately portraying the awkwardness of most first dates and the game that we constantly play in trying to understand the other person’s intentions while adjusting our own expectations. I also think the final 2 stanzas do a really good job of tying the story together as a whole and showing the significance of this date in greater context to the narrator’s character arc, even if it is imperfect in itself.
- {2253} This is such a sweet story! You do such a great job of showing this protagonist’s nerves by outlining that he thinks he’s “boring, average, and shy” in comparison to Dylan, but also why he chooses to overcome it by thinking “it’s now or never…” Great job really showing the character’s motivations to ensure the reader can really connect with them. Well done! Lastly, I really enjoyed the final stanza and the moral around taking a chance when you have it—even if it ends up being short-lived. This is such a great conclusion to the story to keep readers thinking about it. Great job crafting a very engaging and captivating story!
- {1943} Oh my goodness, this was such an endearing, sweet story. Your premise was simple but delightful. I think that any reader would identify with the protagonist’s fears about the date. I smiled at lines such as “I talk too much, or not enough” and “I must be grinning like a fool.” The characterization of this shy man was excellent – we really felt his fear and self-doubt. The depiction of the date was lovely. My heart melted as Dylan relaxed. I loved moments such as “He looks at me, his smile sincere” and “He moves his hand, it’s touching mine.” You left the reader wanting to see more, but equally, I loved the way that you left us feeling that even if this was the end of the romance, the protagonist had learned and grown from being brave. 🙂
WHAT THE JUDGES FEEL NEEDS WORK –
- {2144} I love the story overall and think it’s pretty tightly written, so I don’t have any big notes. My only question is that I couldn’t help wondering why Dylan seems a little reserved throughout most of the date until they get to the park. I wonder if there is a way to hint a little more why that might be the case. Is it because he’s leaving? Does it just take a little bit for him to warm up? i just wanted a little more insight into his character and where this ambivalence comes from.
- {2253} This story would benefit from a bit more exploration around this protagonist’s previous relationship with Dylan. It’s evident that they have had a crush for “so damn long” but what is the current nature of their relationship by the start of the story? For example, had they been friends, but the protagonist wanted to be more than that? Had they never spoken to each other, but just sat next to each other in class, or did Dylan not even know he existed. Showing the nature of their relationship in more specific detail would really help the reader better understand the stakes of what the protagonist has to lose as well as what they are overcoming to ask Dylan out on a date.
- {1943} I thought that your writing was excellent, and I struggled to find much to suggest you might work on. A few points to consider might be: I found the line “I’d gladly pay” a little odd. As I reread, I understood your intention, but it felt awkward, and as if maybe you worded it like this to create the rhyme with ‘anyway/pay’. I would maybe simplify the sentence so we don’t have to think too hard about the implied meaning, especially as this comes right at the start of the story. The line “I suddenly feel very light” seemed rather understated or basic to me. I felt that the focus was on creating a rhyme, and I found myself pausing to consider how it might feel to suddenly feel “light”. Could you create a more sensory description of how he reacted, so that it feels more personal and authentic? I wondered if it would be more meaningful if you devoted the entire final verse to the romance, rather than reverting to the issue of the friends. This removed us from the emotion of the moment.
