This is heavily inspired by @twolegsandbleeds and their Simon can’t flirt series<3 (go read it. It’s amazing.)
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Simon Riley didn’t do soft.
He didn’t do gentle smiles across a room or teasing glances that lingered too long. He didn’t know how to lean against a wall and charm someone with a few well placed words. Those were things other men did—men who grew up in homes where love looked like laughter and warm dinners.
Simon grew up where love looked like broken dishes and bruised knuckles.
So when he realized he liked you, it confused the hell out of him.
It started small. You worked nearby—same building, different department. He’d seen you around enough to recognize the soft way you moved through rooms, like you were trying not to disturb the air. Always polite. Always quiet. Eyes that never quite held his for long.
At first, he thought you avoided him because of the mask.
But then he started noticing other things.
The way you’d freeze when he walked past, shoulders going stiff. The way your fingers would tighten around whatever you were holding. The way you’d duck your head so quickly he barely caught a glimpse of your face.
Simon leaned back in his chair in the rec room one night, arms crossed as he stared at the ceiling.
Still… it didn’t stop the feeling.
It was strange, liking someone. He didn’t know what to do with it. Soap had once said something about flirting—buying drinks, cracking jokes, smiling.
Simon wasn’t about to start cracking jokes.
After two weeks of overthinking it, he came to a conclusion.
All the things he was good at.
So the next morning, when he saw you standing alone near the coffee machine, he decided that was as good a moment as any.
You didn’t notice him at first.
You were focused on the coffee cup in your hands, carefully stirring sugar into it. Humming under your breath as the small spoon clinked softly against the ceramic.
Simon approached like he would a hostile building.
Measured steps. Quiet. Controlled.
When he stopped behind you, his shadow fell across the counter.
Your shoulders stiffened.
Slowly—very slowly—you turned.
Six foot something of silent military presence, broad shoulders filling the small breakroom doorway. His skull mask stared down at you, dark eyes watching from behind it.
Your brain immediately chose panic.
Your hands tightened around the coffee cup like it might protect you.
Simon studied you for a moment.
Not weak. Just… delicate. Like if someone spoke too loudly you might flinch.
He frowned slightly behind the mask.
Your eyes widened immediately.
Why was this harder than interrogation?
“You’re the one who works down the hall.”
Your voice came out soft and nervous.
He rubbed the back of his neck, clearly uncomfortable.
You looked like you were about two seconds from apologizing yourself into the floor.
Simon straightened slightly, forcing himself to just say it.
His tone was blunt. Matter-of-fact.
“I want to take you out.”
Your brain completely short-circuited.
Simon nodded once, like he was confirming a mission objective.
“Dinner. Or coffee.” He gestured vaguely at the machine. “Whatever people do.”
Your face slowly turned pink.
Simon misread your silence immediately.
Why would someone like you want anything to do with someone like him.
“You don’t have to,” he said quickly, voice flattening into its usual military tone. “Was just askin’. Forget it.”
And that’s when you panicked.
You were gripping your coffee cup with both hands, face red, eyes wide like a deer caught in headlights.
“I mean—” you swallowed hard. “I—I’d like that.”
You were clearly terrified.
Fidgeting. Avoiding his gaze. Nervous energy practically vibrating off you.
Something unfamiliar settled quietly in his chest.
Finally you asked softly, “S-so… when?”
Simon considered it like he was planning a tactical operation.
You looked like you might faint.
Then, after a moment, he added gruffly,
Your head snapped up in surprise.
Simon rubbed the back of his neck again, clearly uncomfortable.
Your expression softened just a little.
And for the first time since the conversation started…
Simon felt something in his chest do a strange, unfamiliar flip.
Maybe this whole flirting thing wasn’t as hard as he thought.
